US3380923A - Germicidal compositions - Google Patents

Germicidal compositions Download PDF

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US3380923A
US3380923A US507666A US50766665A US3380923A US 3380923 A US3380923 A US 3380923A US 507666 A US507666 A US 507666A US 50766665 A US50766665 A US 50766665A US 3380923 A US3380923 A US 3380923A
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parts
surfactant
iodine
water
phosphoric acid
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Martin D Beach
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Whitmoyer-Reed Ltd
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    • 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
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds

Definitions

  • This invention is concerned with germicidal detergent compositions, including compositions known as iodophors, an iodophor being a com-position containing iodine and a carrier in which the carrier is a compound which increases the solubility of iodine in aqueous systems.
  • the iodine is apparently chemically bound to, and/ or complexed with, the carrier.
  • iodophors those comprising iodine and a surfactant.
  • these iodophors are frequently formulated with phosphoric acid to yield aqueous concentrates which are finally diluted with water by the end-user.
  • iodophors in their diluted ready-to-use form should possess a low iodine vapour pressure combined with a high and constant available iodine content, by which is meant that at least 50% of the total iodine present should be titratable with thiosulphate solution and that this titratable quantity should remain constant over a period of time.
  • iodophors which possess the above characteristics to a marked degree in comparison with many iodophors based on conventional surfactants, such as non-ionic surfactants, can be made by using a surfactant having amphoteric properties.
  • the present invention provides a germicidal detergent composition containing iodine and a water-soluble amphoteric surfactant.
  • the composition is preferably in the form of a homogeneous liquid or semi-solid solution which advantageously is an aqueous solution also containing phosphoric acid.
  • the compositions may contain one or more additional nonamphoteric, e.g., anionic or non-ionic, surfactants if these are required to confer additional detergency or to act as clarifying agents if the composition in their diluted form should show a tendency towards cloudiness.
  • a low molecular weight alcohol such as isopropyl alcohol may also be included as a clarifying agent.
  • amphoteric surfactants those preferred are alkylene oxide condensates containing groups which impart amphoteric properties, e.g., amine and sulfate groups.
  • alkylene oxide condensates containing groups which impart amphoteric properties e.g., amine and sulfate groups.
  • examples of such surfactants which have been found to be of special utility, are those comprising mixtures of compounds of the formula:
  • R R and R are alkyl groups containing a total of 7 to 24 carbon atoms, R, is hydrogen or C -C alkyl, particularly methyl, m is an integer and X is hydrogen or 3,380,923 Patented Apr. 30, 1968 an alkali metal, preferably sodium, the mixture containing an average of 6-100, and preferably 12-50 groups per molecule.
  • compounds of the above formula are ethylene oxide derivatives in which case R, will be hydrogen exclusively; but the compounds may be derived from other alkylene oxides, e. g. mixtures of ethylene and propylene oxides. It is also preferred that compounds of the above formula be derived from isomeric mixtures of amines of the formula ial Rn-Cf-NH:
  • surfactants of the class just described are of particular utility in forming ready-for-use germicidal compositions of low iodine vapour pressure combined with a high and constant available iodine content.
  • amphoteric surfactants are those of the classes set forth below:
  • Amino-substituted alkanoic acids and salts thereof such as those containing from 2 to about 8 carbon atoms in the alkanoic acid portion and having as a substituent an amino group whose remaining two valences are satisfied by hydrogen and a C3-C18 hydrocarbon or acyl group.
  • a typical sub-class of such compounds is represented by the formula:
  • R represents a surface activity producing group with 8 to 18 or more carbon atoms and M is a salt-forming cation or hydrogen.
  • Betaine type of compounds such as betaine derivatives of the formula:
  • R is as defined above and R R and R are shorter chain alkyl (or alkylene in the case of R groups, e.g. methyl or methylene.
  • the weight ratio of amphoteric surfactant to iodine will range from 1:1 to 50:1, and preferably ranges from 2:1 to 10: 1.
  • the amount of iodine in a concentrate intended to be diluted by the end-user will gen erally be from 0.5 to 6% by weight, preferably 1 to 3% and the amount of amphoteric surfactant in this type of composition will generally range from 2 to 25% by weight.
  • concentrates for dilution with water by the end-user will generally contain the equivalent of about 2 to 5 0% by Weight, typically 4 to 30% by weight, phosphoric acid.
  • non-amphoteric surfactant may be one of the conventional non-ionic materials such as condensates of an alkylene oxide, e.g., ethylene and/ or propylene oxide, and a hydrophobic compound containing an active hydrogen atom.
  • Preferred non-ionic surfactants are condensates of octyl or nonyl phenol and 6 to moles of ethylene oxide.
  • anionic surfactants such as sulfonated or sulfated materials.
  • Surfactant A is a mixture of amphoteric compounds of the formula:
  • residues are derived from a commercial mixture of isomeric amines having 12-15 carbon atoms and exhibiting a tertiary alkyl structure at the point of attachment to the amino nitrogen atom and m is an integer; there being an average of 15 CH CH O- groups per mole of amphoteric compound.
  • Surfactant B is a non-ionic condensate of otcylphenol and 9-10 moles of ethylene oxide.
  • R B1-NR3CO0- R4 where R represents long chain alkyl, at least 90% of such alkyl radicals being dodecyl, R and R are methyl and R is methylene.
  • Surfactant D is a product available as Ambiteric H and is similar to Ambiteric D described above except that at least 90% of the R alkyl radicals are hexadecyl.
  • Surfactant E is a product available commercially as Deriphat 1700 from General Mills, Inc., Illinois, United States of America. This product contains ca. 50% N- lauryl myristyl B-aminopropionic acid.
  • Surfactant F is a product available commercially as Empigen BB from Marchon Products Ltd, Whitehaven, England; it contains 30% active ingredient which is similar to the active component in Surfactant C described above except that the R radicals are predominantly lauryl/myristyl.
  • Example I There are intimately mixed 3.5 parts of iodine and 20 parts of Surfactant A to form a homogeneous iodophor which can be formulated into a germicidal concentrate for the dairy and poultry industries.
  • Example 11 23.5 parts of the iodophor of Example I are mixed with 50 parts of phosphoric acid (85%) and water is added to make 125 parts. The product on dilution with water forms an excellent germicidal detergent which passes the test described by Hoy et al. in the Journal of Applied Bacteriology 23 (2), pp. 359-371 and which is therefore.
  • Example III There are intimately mixed 3.5 parts of iodine and parts of Surfactant A. To the iodophor thus made are 4 added 5 parts phosphoric acid 7 parts of Surfactant B and water to make a total of parts. There results a germicidal detergent composition suitable for use in the poultry industry after suitable dilution with water.
  • Example V There are intimately mixed 3.5 parts of iodine and 10 parts of Surfactant A and to the iodophor thus obtained there are added 50 parts phosphoric acid (85 7 parts of Surfactant B and water to make 100 parts. There results a germicidal detergent composition useful in the dairy industry after dilution with water.
  • Example VI There are intimately mixed 3.5 parts of iodine and 12 parts of Surfactant C to form an iodophor. There are then added 5 parts of phosphoric acid (85%), 12 parts of Surfactant B and water to make parts. The product is suitable as a germicide for the poultry industry after dilution with water.
  • Part (a) is repeated except that an additional 45 parts of phosphoric acid (85%) are added.
  • the product is suitable for the dairy industry after dilution.
  • Example VII (a) There are intimately mixed 5 parts of iodine and 30 parts of Surfactant E to form an iodophor. There are then added 7.5 parts of phosphoric acid (85% 20 parts of Surfactant B and water to make parts. The product is a germicide suitable for use in the poultry industry.
  • Part (a) is repeated except that 75 parts of phosphoric acid (85 are added and water is added to make 200 parts.
  • the product is suitable for use in the dairy industry after dilution with water.
  • Example VIII There are intimately mixed 5 parts of iodine and 45 parts of Surfactant F to form an iodophor. To the iodophor are added 7.5 parts of phosphoric acid (85 20 parts of Surfacant B, 10 parts isopropyl alcohol and water to make 180 parts. The product is suitable for use in the poultry industry.
  • Part (a) is repeated except that 75 parts of phosphoric acid (85%) are used and water is added to make 210 parts.
  • the product is useful in the dairy industry after dilution with water.
  • An iodophor composition consisting essentially of iodine and, as water-soluble amphoteric surfactant, a mixture of compounds of the formula:
  • R R and R are alkyl groups containing a total of 7 to 24 carbon atoms, R; is selected from the group consisting of hydrogen and alkyl groups having 1 to 4 carbon atoms, m is an integer having an average value of 6 to 100 and X is selected from the group consisting of hydrogen and the alkalimetals, the weight ratio of surfactant to iodine ranging from 1:1 to 50:1.
  • composition according to claim 1 wherein R is hydrogen, X is sodium and the mixture contains an average of 12 to 50 -(CH CH O)- groups per molecule.
  • composition according to claim 1 wherein the weight ratio of surfactant to iodine is from 2:1 to 10:1.
  • a concentrate for dilution with water to form a germicidal detergent composition which consists essentially of iodine, phosphoric acid and, as amphoteric surfactant, a mixture of compounds of the formula:
  • R R and R are alkyl groups containing a total 5 of 7 to 24 carbon atoms, R; is selected from the group consisting of hydrogen and alkyl groups having from 1 to 4 carbon atoms, m is an integer having an average value of 6 to 100 and X is selected from the group consisting of hydrogen and the alkali metals, the weight ratio of surfactant to iodine ranging from 1:1 to 50:1.
  • a concentrate according to claim 4 which contains 0.5 to 6% by weight of iodine and wherein the weight ratio of surfactant to iodine is from 2:1 to 10:1.
  • a concentrate according to claim 4 which contains the equivalent of 2 to 50% by weight of 85% phosphoric acid.
  • a concentrate according to claim 4 which also contains a nonionic surfactant comprising a condensate of an alkylene oxide and a hydrophobic compound containing an active hydrogen atom.

Description

United States Patent 3,380,923 GERMICIDAL CGB/iPOSiTlUNS Martin D. Beach, London, England, assignor to Whitmoyer-Reed Limited, Barking, Essex, Engiand, a British company No Drawing. Filed Nov. 15, 1965, Ser. No. 507,666 Claims priority, application Great Britain, Nov. 16, 1964, 46,499/64 7 Claims. (Cl. 252-106) ABSTRACT OF THE DISCLOSURE Disclosed herein are certain germicidal detergent compositions, and particularly, iodophors wherein the iodine carrier is an alkylene oxide condensate having amphoteric properties. Such germicides are especially suitable for the poultry and dairy industry.
This invention is concerned with germicidal detergent compositions, including compositions known as iodophors, an iodophor being a com-position containing iodine and a carrier in which the carrier is a compound which increases the solubility of iodine in aqueous systems.
In an iodophor, the iodine is apparently chemically bound to, and/ or complexed with, the carrier.
Among the known iodophors are those comprising iodine and a surfactant. To form germicidal compositions, these iodophors are frequently formulated with phosphoric acid to yield aqueous concentrates which are finally diluted with water by the end-user.
A most important characteristic of iodophors in their diluted ready-to-use form is that they should possess a low iodine vapour pressure combined with a high and constant available iodine content, by which is meant that at least 50% of the total iodine present should be titratable with thiosulphate solution and that this titratable quantity should remain constant over a period of time.
It has now been found that iodophors which possess the above characteristics to a marked degree in comparison with many iodophors based on conventional surfactants, such as non-ionic surfactants, can be made by using a surfactant having amphoteric properties.
Based on the above discovery, the present invention provides a germicidal detergent composition containing iodine and a water-soluble amphoteric surfactant. The composition is preferably in the form of a homogeneous liquid or semi-solid solution which advantageously is an aqueous solution also containing phosphoric acid. The compositions may contain one or more additional nonamphoteric, e.g., anionic or non-ionic, surfactants if these are required to confer additional detergency or to act as clarifying agents if the composition in their diluted form should show a tendency towards cloudiness. A low molecular weight alcohol such as isopropyl alcohol may also be included as a clarifying agent.
Whilst many amphoteric surfactants can be used, those preferred are alkylene oxide condensates containing groups which impart amphoteric properties, e.g., amine and sulfate groups. Examples of such surfactants, which have been found to be of special utility, are those comprising mixtures of compounds of the formula:
where R R and R are alkyl groups containing a total of 7 to 24 carbon atoms, R, is hydrogen or C -C alkyl, particularly methyl, m is an integer and X is hydrogen or 3,380,923 Patented Apr. 30, 1968 an alkali metal, preferably sodium, the mixture containing an average of 6-100, and preferably 12-50 groups per molecule. Preferably, compounds of the above formula are ethylene oxide derivatives in which case R, will be hydrogen exclusively; but the compounds may be derived from other alkylene oxides, e. g. mixtures of ethylene and propylene oxides. It is also preferred that compounds of the above formula be derived from isomeric mixtures of amines of the formula ial Rn-Cf-NH:
and which contain 12 to 24 carbon atoms, e.g. mixtures of amines containing 12 to 15 carbon atoms or 18 to 24 carbon atoms. Surfactants of the class just described are of particular utility in forming ready-for-use germicidal compositions of low iodine vapour pressure combined with a high and constant available iodine content.
Other usable amphoteric surfactants are those of the classes set forth below:
1) Amino-substituted alkanoic acids and salts thereof, such as those containing from 2 to about 8 carbon atoms in the alkanoic acid portion and having as a substituent an amino group whose remaining two valences are satisfied by hydrogen and a C3-C18 hydrocarbon or acyl group. A typical sub-class of such compounds is represented by the formula:
where R represents a surface activity producing group with 8 to 18 or more carbon atoms and M is a salt-forming cation or hydrogen.
(2) Betaine type of compounds such as betaine derivatives of the formula:
where R is as defined above and R R and R are shorter chain alkyl (or alkylene in the case of R groups, e.g. methyl or methylene.
(3) Compounds having the formula:
R N(CH CH O OM 2 where R is as defined above and M is a salt-forming cation or hydrogen.
In general, the weight ratio of amphoteric surfactant to iodine will range from 1:1 to 50:1, and preferably ranges from 2:1 to 10: 1. The amount of iodine in a concentrate intended to be diluted by the end-user will gen erally be from 0.5 to 6% by weight, preferably 1 to 3% and the amount of amphoteric surfactant in this type of composition will generally range from 2 to 25% by weight.
When, as is preferred, phosphoric acid is present, concentrates for dilution with water by the end-user will generally contain the equivalent of about 2 to 5 0% by Weight, typically 4 to 30% by weight, phosphoric acid.
If a non-amphoteric surfactant is included in the composition such surfactant may be one of the conventional non-ionic materials such as condensates of an alkylene oxide, e.g., ethylene and/ or propylene oxide, and a hydrophobic compound containing an active hydrogen atom. Preferred non-ionic surfactants are condensates of octyl or nonyl phenol and 6 to moles of ethylene oxide. Alternatively there may be used anionic surfactants such as sulfonated or sulfated materials.
3 The invention is illustrated by the following examples in which Surfactants A-F are those identified below:
Surfactant A is a mixture of amphoteric compounds of the formula:
residues are derived from a commercial mixture of isomeric amines having 12-15 carbon atoms and exhibiting a tertiary alkyl structure at the point of attachment to the amino nitrogen atom and m is an integer; there being an average of 15 CH CH O- groups per mole of amphoteric compound.
Surfactant B is a non-ionic condensate of otcylphenol and 9-10 moles of ethylene oxide.
Surfactant C is a product available commercially as Ambiteric D from Glovers (Chemicals) Ltd, Leeds, England; it is believed to consist predominantly (=8590%) of molecules of the formula:
R B1-NR3CO0- R4 where R represents long chain alkyl, at least 90% of such alkyl radicals being dodecyl, R and R are methyl and R is methylene.
Surfactant D is a product available as Ambiteric H and is similar to Ambiteric D described above except that at least 90% of the R alkyl radicals are hexadecyl.
Surfactant E is a product available commercially as Deriphat 1700 from General Mills, Inc., Illinois, United States of America. This product contains ca. 50% N- lauryl myristyl B-aminopropionic acid.
Surfactant F is a product available commercially as Empigen BB from Marchon Products Ltd, Whitehaven, England; it contains 30% active ingredient which is similar to the active component in Surfactant C described above except that the R radicals are predominantly lauryl/myristyl.
In the examples which now follow parts and percentages are on a weight basis and in all instances the iodophors described were made by mixing the iodine'and the amphoteric surfactant at a temperature of 35 C. and for a sufiicient time to result in the iodophor.
Example I There are intimately mixed 3.5 parts of iodine and 20 parts of Surfactant A to form a homogeneous iodophor which can be formulated into a germicidal concentrate for the dairy and poultry industries.
Example 11 23.5 parts of the iodophor of Example I are mixed with 50 parts of phosphoric acid (85%) and water is added to make 125 parts. The product on dilution with water forms an excellent germicidal detergent which passes the test described by Hoy et al. in the Journal of Applied Bacteriology 23 (2), pp. 359-371 and which is therefore.
particularly suited for use in the diary industry.
Example III There are intimately mixed 3.5 parts of iodine and parts of Surfactant A. To the iodophor thus made are 4 added 5 parts phosphoric acid 7 parts of Surfactant B and water to make a total of parts. There results a germicidal detergent composition suitable for use in the poultry industry after suitable dilution with water.
Example V There are intimately mixed 3.5 parts of iodine and 10 parts of Surfactant A and to the iodophor thus obtained there are added 50 parts phosphoric acid (85 7 parts of Surfactant B and water to make 100 parts. There results a germicidal detergent composition useful in the dairy industry after dilution with water.
Example VI (a) There are intimately mixed 3.5 parts of iodine and 12 parts of Surfactant C to form an iodophor. There are then added 5 parts of phosphoric acid (85%), 12 parts of Surfactant B and water to make parts. The product is suitable as a germicide for the poultry industry after dilution with water.
(b) Part (a) is repeated except that Surfactant C is replaced by the same quantity of Surfactant D, 10 parts of the water is replaced by 10 parts of isopropyl alcohol and an additional 8 parts of Surfactant B are added.
(0) Part (a) is repeated except that an additional 45 parts of phosphoric acid (85%) are added. The product is suitable for the dairy industry after dilution.
Example VII (a) There are intimately mixed 5 parts of iodine and 30 parts of Surfactant E to form an iodophor. There are then added 7.5 parts of phosphoric acid (85% 20 parts of Surfactant B and water to make parts. The product is a germicide suitable for use in the poultry industry.
(b) Part (a) is repeated except that 75 parts of phosphoric acid (85 are added and water is added to make 200 parts. The product is suitable for use in the dairy industry after dilution with water.
Example VIII (a) There are intimately mixed 5 parts of iodine and 45 parts of Surfactant F to form an iodophor. To the iodophor are added 7.5 parts of phosphoric acid (85 20 parts of Surfacant B, 10 parts isopropyl alcohol and water to make 180 parts. The product is suitable for use in the poultry industry.
(b) Part (a) is repeated except that 75 parts of phosphoric acid (85%) are used and water is added to make 210 parts. The product is useful in the dairy industry after dilution with water.
I claim:
1. An iodophor composition consisting essentially of iodine and, as water-soluble amphoteric surfactant, a mixture of compounds of the formula:
where R R and R are alkyl groups containing a total of 7 to 24 carbon atoms, R; is selected from the group consisting of hydrogen and alkyl groups having 1 to 4 carbon atoms, m is an integer having an average value of 6 to 100 and X is selected from the group consisting of hydrogen and the alkalimetals, the weight ratio of surfactant to iodine ranging from 1:1 to 50:1.
2. A composition according to claim 1, wherein R is hydrogen, X is sodium and the mixture contains an average of 12 to 50 -(CH CH O)- groups per molecule.
3. A composition according to claim 1; wherein the weight ratio of surfactant to iodine is from 2:1 to 10:1.
4. A concentrate for dilution with water to form a germicidal detergent composition which consists essentially of iodine, phosphoric acid and, as amphoteric surfactant, a mixture of compounds of the formula:
where R R and R are alkyl groups containing a total 5 of 7 to 24 carbon atoms, R; is selected from the group consisting of hydrogen and alkyl groups having from 1 to 4 carbon atoms, m is an integer having an average value of 6 to 100 and X is selected from the group consisting of hydrogen and the alkali metals, the weight ratio of surfactant to iodine ranging from 1:1 to 50:1.
5. A concentrate according to claim 4 which contains 0.5 to 6% by weight of iodine and wherein the weight ratio of surfactant to iodine is from 2:1 to 10:1.
6. A concentrate according to claim 4 which contains the equivalent of 2 to 50% by weight of 85% phosphoric acid.
7. A concentrate according to claim 4 which also contains a nonionic surfactant comprising a condensate of an alkylene oxide and a hydrophobic compound containing an active hydrogen atom.
References Cited UNITED STATES PATENTS 3,291,692 12/1966 Hagerty 252107 3,277,010 10/1966 Schenck et a1. 252l06 LEON D. ROSDOL, Primary Examiner.
S. E. DARDEN, S. D. SCHNEIDER,
Assistant Examiners.
UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No 3 ,380 ,923 April 50 1968 Martin D. Beach It is certified that error appears in the above identified patent and that said Letters Patent are hereby corrected as shown below:
Column 2, lines 32 and 33, the formula should appear as shown below:
R N(CH CH COOM) Column 3, lines 26 to 29, the formula should appear as shown below:
Signed and sealed this 16th day of December 1969.
(SEAL) Attest:
EDWARD M.FLETCHER,JR. WILLIAM E. SCHUYLER, JR. Attesting Officer Commissioner of Patents
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3525696A (en) * 1966-04-25 1970-08-25 West Laboratories Inc Low-foaming germicidal surfactantiodine compositions for cleaned-inplace equipment
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
US4206204A (en) * 1974-11-29 1980-06-03 Tenneco Chemicals, Inc. Iodophor compositions containing tertiary amine oxides
US4207310A (en) * 1974-11-29 1980-06-10 Tenneco Chemicals, Inc. Iodine-amine oxide disinfectants
US4597975A (en) * 1981-11-06 1986-07-01 Woodward Fred E Iodine surface active compositions
US4908147A (en) * 1986-02-19 1990-03-13 Ciba-Geigy Corporation Aqueous self preserving soft contact lens solution and method
US5049299A (en) * 1989-10-26 1991-09-17 Kiwi Brands Incorporated Liquid lavatory cleansing and sanitizing composition
US5344811A (en) * 1989-10-26 1994-09-06 Kiwi Brands Inc Method for dispensing compositions in an aqueous system
WO2000018867A1 (en) * 1998-09-25 2000-04-06 The Procter & Gamble Company Antimicrobial detergent compositions
WO2000057703A1 (en) * 1999-03-26 2000-10-05 Ecolab Inc. Antimicrobial and antiviral compositions containing an oxidizing species
US6534075B1 (en) 1999-03-26 2003-03-18 Ecolab Inc. Antimicrobial and antiviral compositions and treatments for food surfaces
US20030175503A1 (en) * 2002-01-16 2003-09-18 3M Innovative Properties Company Pressure sensitive adhesives having quaternary ammonium functionality, articles, and methods
US20030185902A1 (en) * 2002-03-28 2003-10-02 Ecolab Inc. Antimicrobial and antiviral compositions containing an oxidizing species
US20030194447A1 (en) * 2002-01-16 2003-10-16 3M Innovative Properties Company Antiseptic compositions and methods
US20030194415A1 (en) * 2002-01-16 2003-10-16 3M Innovative Properties Company Film-forming compositions and methods

Citations (2)

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Publication number Priority date Publication date Assignee Title
US3277010A (en) * 1963-06-26 1966-10-04 Gen Aniline & Film Corp Iodine detergent compositions
US3291692A (en) * 1965-05-26 1966-12-13 Grace W R & Co Germicidal compositions containing complexes of iodine

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3277010A (en) * 1963-06-26 1966-10-04 Gen Aniline & Film Corp Iodine detergent compositions
US3291692A (en) * 1965-05-26 1966-12-13 Grace W R & Co Germicidal compositions containing complexes of iodine

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3525696A (en) * 1966-04-25 1970-08-25 West Laboratories Inc Low-foaming germicidal surfactantiodine compositions for cleaned-inplace equipment
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
US4206204A (en) * 1974-11-29 1980-06-03 Tenneco Chemicals, Inc. Iodophor compositions containing tertiary amine oxides
US4207310A (en) * 1974-11-29 1980-06-10 Tenneco Chemicals, Inc. Iodine-amine oxide disinfectants
US4597975A (en) * 1981-11-06 1986-07-01 Woodward Fred E Iodine surface active compositions
US4908147A (en) * 1986-02-19 1990-03-13 Ciba-Geigy Corporation Aqueous self preserving soft contact lens solution and method
US5049299A (en) * 1989-10-26 1991-09-17 Kiwi Brands Incorporated Liquid lavatory cleansing and sanitizing composition
US5344811A (en) * 1989-10-26 1994-09-06 Kiwi Brands Inc Method for dispensing compositions in an aqueous system
WO2000018867A1 (en) * 1998-09-25 2000-04-06 The Procter & Gamble Company Antimicrobial detergent compositions
WO2000057703A1 (en) * 1999-03-26 2000-10-05 Ecolab Inc. Antimicrobial and antiviral compositions containing an oxidizing species
US6436445B1 (en) 1999-03-26 2002-08-20 Ecolab Inc. Antimicrobial and antiviral compositions containing an oxidizing species
US6534075B1 (en) 1999-03-26 2003-03-18 Ecolab Inc. Antimicrobial and antiviral compositions and treatments for food surfaces
US20030175503A1 (en) * 2002-01-16 2003-09-18 3M Innovative Properties Company Pressure sensitive adhesives having quaternary ammonium functionality, articles, and methods
US20030194447A1 (en) * 2002-01-16 2003-10-16 3M Innovative Properties Company Antiseptic compositions and methods
US20030194415A1 (en) * 2002-01-16 2003-10-16 3M Innovative Properties Company Film-forming compositions and methods
US6838078B2 (en) 2002-01-16 2005-01-04 3M Innovative Properties Company Film-forming compositions and methods
US20050025794A1 (en) * 2002-01-16 2005-02-03 3M Innovative Properties Company Film-forming compositions and methods
US7005031B2 (en) 2002-01-16 2006-02-28 3M Innovative Properties Company Pressure sensitive adhesives having quaternary ammonium functionality, articles, and methods
US20060177511A1 (en) * 2002-01-16 2006-08-10 3M Innovative Properties Company Antiseptic compositions and methods
US7147873B2 (en) * 2002-01-16 2006-12-12 3M Innovative Properties Company Antiseptic compositions and methods
US7323163B2 (en) 2002-01-16 2008-01-29 3M Innovative Properties Company Film-forming compositions and methods
US8840932B2 (en) 2002-01-16 2014-09-23 3M Innovative Properties Company Antiseptic compositions and methods
US9277750B2 (en) 2002-01-16 2016-03-08 3M Innovative Properties Company Antiseptic compositions and methods
US20030185902A1 (en) * 2002-03-28 2003-10-02 Ecolab Inc. Antimicrobial and antiviral compositions containing an oxidizing species
US6855328B2 (en) 2002-03-28 2005-02-15 Ecolab Inc. Antimicrobial and antiviral compositions containing an oxidizing species

Also Published As

Publication number Publication date
BE672353A (en) 1966-03-16
FR1453772A (en) 1966-06-03
DE1467703A1 (en) 1969-11-13
BR6574847D0 (en) 1973-09-06
DK113597B (en) 1969-04-08
NL6514862A (en) 1966-05-17
GB1120230A (en) 1968-07-17

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