US3069358A - Germicidal detergent composition - Google Patents
Germicidal detergent composition Download PDFInfo
- Publication number
- US3069358A US3069358A US723942A US72394258A US3069358A US 3069358 A US3069358 A US 3069358A US 723942 A US723942 A US 723942A US 72394258 A US72394258 A US 72394258A US 3069358 A US3069358 A US 3069358A
- Authority
- US
- United States
- Prior art keywords
- detergent composition
- hexachlorophene
- germicidal
- parts
- germicidal detergent
- 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
- 239000003599 detergent Substances 0.000 title description 18
- 239000000203 mixture Substances 0.000 title description 17
- 230000002070 germicidal effect Effects 0.000 title description 14
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 17
- 229960004068 hexachlorophene Drugs 0.000 description 16
- 229930193140 Neomycin Natural products 0.000 description 6
- 229960004927 neomycin Drugs 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000344 soap Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- LIFHMKCDDVTICL-UHFFFAOYSA-N 6-(chloromethyl)phenanthridine Chemical compound C1=CC=C2C(CCl)=NC3=CC=CC=C3C2=C1 LIFHMKCDDVTICL-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000013504 Triton X-100 Substances 0.000 description 2
- 229920004890 Triton X-100 Polymers 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- PGBHMTALBVVCIT-VCIWKGPPSA-N framycetin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VCIWKGPPSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940053050 neomycin sulfate Drugs 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- IDOQDZANRZQBTP-UHFFFAOYSA-N 2-[2-(2,4,4-trimethylpentan-2-yl)phenoxy]ethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1OCCO IDOQDZANRZQBTP-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- QZXSMBBFBXPQHI-UHFFFAOYSA-N N-(dodecanoyl)ethanolamine Chemical compound CCCCCCCCCCCC(=O)NCCO QZXSMBBFBXPQHI-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229920004929 Triton X-114 Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 1
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 1
- 229940074323 antara Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- MKHVZQXYWACUQC-UHFFFAOYSA-N bis(2-hydroxyethyl)azanium;dodecyl sulfate Chemical compound OCCNCCO.CCCCCCCCCCCCOS(O)(=O)=O MKHVZQXYWACUQC-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- GBEYVKHMIPVAHD-UHFFFAOYSA-M potassium;hexadecyl sulfate Chemical compound [K+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GBEYVKHMIPVAHD-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
Description
United States Patent G 3,069,358 GERMICIDAL DETERGENT COMPOSITION Jack Blodinger, Monsey, N.Y., assignor to American Cyanamid Company, New York, N.Y., a corporation of Maine No Drawing. Filed Mar. 26, 1958, Ser. No. 723,942 1 Claim. (Cl. 252107) This invention relates to a germicidal detergent composition containing hexachlorophene.
Hexachlorophene [2,2' methylenebis( 3,4,6 trichlorophenol)] is a well-known germicidal agent and has been used in soaps and various soap preparations. It is known that hexachlorophene is practically insoluble in water. It can be dissolved by the use of strong alkali resulting in solutions having a pH well above pH 9. Hexachlorophene can also be dissolved by the addition to soaps which have a pH above about 9. A solution of such high alkalinity, however, has a deleterious effect on the skin and frequent washings with such germicidal soaps or solutions can cause severe irritation of the skin.
It would be highly desirable to be able to prepare a germicidal detergent composition containing hexachlorophene in solution which would have a pH near that of the body, that is a pH of about S-7, but heretofore this has not been possible because hexachlorophene is not soluble at such relatively low hydrogen ion concentrations.
I have now discovered a Way of preparing germicidal detergent compositions containing hexachlorophene in solution at a desirably low pH of about -7 and in which the hexachlorophene is rendered soluble by the addition thereto of a certain specific class of nonionic surface active agents.
In carrying out the present invention, hexachlorophene is first dissolved in a nonionic surface active agent of the type described more particularly hereinafter. Preferably the hexachlorophene is dissolved in the nonionic detergent by heating at a temperature of from about 50 to 70 C. The resulting clear solution is then diluted with water to the desired concentration. A stable, germicidal solution is obtained which is stable even after adjusting the pH to between about 5'-7 if necessary. The hexachlorophene is usually present to the extent of between about /2 and 5% by weight.
It is also within the scope of the present invention to incorporate a small amount of the antibiotic known as neomycin (cf. United States patent to Waksman No. 2,799,620) into the detergent composition. The nonionic surface active agent apparently renders the neomycin compatible with such solutions and prevents precipitation of the neomycin which normally occurs in such compositions when the pH is around neutrality. Usually a small amount, from about 0.1 to about 3%, of neomycin sufiices for purposes of obtaining the additional bacteriostatic effect.
Among the suitable anionic detergents are the watersoluble higher fatty acid soaps (e.g. sodium lauryl sulfate, sodium salts of higher fatty acids derived from coconut oil, palm oil and tallow), and the sulfated and sulfonated organic detergents. Examples of the latter are water-soluble salts of higher alkyl aryl sulfonate (e.g. sodium dodecylbenzenesulfonate, sodium laurylbenzenesulfonate), higher alkyl sulfate detergent (e.g. sodium lauryl sulfate, potassium cetyl sulfate, triethanolamine lauryl sulfate, diethanolamine lauryl sulfate and ammonium lauryl sulfate), sulfuric acid esters of polyhydric alcohols incompletely esterified with higher fatty acids (e.g. sodium coconut monoglyceride monosulfate), sulfated higher fatty acid amides (e.g. sodium lauric monoethanolamide sulfate), etc. The anionic detergent is added for the purpose of increasing the detergency of the ICC formula:
CaHry-(O 011,011,) .on
and wherein n is from 6-30, and the nonylphenoxypolyoxyethylene compounds sold under the trademark Igepal and corresponding to the formula:
ogmwgwomonnnon wherein n is from 6-30. The nonionic surface active agent is usually employed in an amount ranging from about 1 to 40% by weight.
The invention will be described in greater detail in conjunction with the following specific examples in which the parts are by Weight unless otherwise specified.
Example 1 A germicidal detergent composition is prepared'by dissolving five parts of hexachlorophene in 10 parts by volume of Triton X-l00 (reaction product of 9-10 moles of ethylene oxide with octylphenol) with heating at 60 to C. The resulting clear solution is added to parts by volume of water with stirring. A clear solution results and shows no change on standing for long periods of time at 5 C.
Example 2 A germicidal detergent composition is prepared by dissolving 0.15 part of neomycin sulfate in 40 parts by volume of water. 5 parts of hexachlorophene are dissolved in 10 parts by volume of Triton X400. The hexachlorophene solution is added to the neomycin solution and 10 parts by volume of Triton X-l14 (reaction product of 7-8 moles of ethylene oxide with octylphenol) are added along with 2.5 parts of Lanogel 41 (a watersoluble derivative of lanolin) and 20 parts by volume of triethanolamine lauryl sulfate. Distilled water is added to bring the volume up to 100 parts. A clear sparkling yellow solution with a pH of 5.5 is obtained. The resulting solution is stable as to the neomycin and hexachlorophene for a period of at least one year at a temperature of 25 C. and for two months at 42 C. or for one week at 56 C.
Example 3 A germicidal detergent composition is prepared as in Example 2 except that Triton X-114 is omitted. A storage stable composition is obtained.
Example 4 A germicidal detergent composition is prepared as in Example 2 except that Triton X-100 is omitted. A storage stable detergent composition is obtained.
Example 5 A germicidal detergent composition is prepared as in Example 2 except that 8 parts of Igepal CO-710 (nonylphenoxypolyoxyethylene) is used in place of the Triton X-100 used in Example 2. A storage stable composition is obtained.
I claim:
A germicidal detergent composition consisting essentially of from about 1 to about 40% of a nonionic surface from about 0.1 to about 3% of a therapeutically effective,
form of neornycin, and suflicient Water to total 100%, the resulting composition having a pH of between about 5 and about 7, and being storage stable for at least about a year at 25 C.
References Cited in the file of this patent UNITED STATES PATENTS 2,303,932 Guild Dec. 1, 1942 2,484,784 Craige et a1 Oct. 11, 1949 2,865,859 Lubowe Dec. 23, 1958 2,880,130 Johnson Mar. 31, 1959 2,880,138 Johnson Mar. 31, 1959 2,942,008 Lubowe June 21, 1960 2,961,375 Shaw Nov. 22, 1960 2,968,628 Reed Ian. 17, 1961 2,975,099 Goyan et al Mar. 14, 1961 2,979,410 Parlour Apr. 11, 1961 3,029,188 Cyr et al. Apr. 10, 1962 FOREIGN PATENTS 761,269 Great Britain Nov. 14, 1956 OTHER REFERENCES NNR, New and Nonofiicial Remedies, 1955, Lippincott Co., Philadelphia, Pa., p. 71.
American Drug Index, Lippincott Co., Philadelphia, Pa. (1956), p. 380.
Antarox A200, Antara Products, General Aniline and Film Corp. New York (1950), 6 p. brochure, p. 6 relied upon.
Gregg et al.: J.A.P.A., Sci. Ed., vol. 40, Solubility and Bacterial Studies of Hexachlorophene, August 1951, pp. 390 et seq.
Traub: Arch. Dermatol. and SyphiloL, vol. 52, 1945, p. 385.
Dale: J.A.P.A., Prac. Pharm. Ed., July 1957, Compatibility of Neomycin Sulfate, pp. 421-425.
Protosil: J.A.P.A. Prac. Pharm. Ed., August 1956, p. 547.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US723942A US3069358A (en) | 1958-03-26 | 1958-03-26 | Germicidal detergent composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US723942A US3069358A (en) | 1958-03-26 | 1958-03-26 | Germicidal detergent composition |
Publications (1)
Publication Number | Publication Date |
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US3069358A true US3069358A (en) | 1962-12-18 |
Family
ID=24908331
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US723942A Expired - Lifetime US3069358A (en) | 1958-03-26 | 1958-03-26 | Germicidal detergent composition |
Country Status (1)
Country | Link |
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US (1) | US3069358A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3174905A (en) * | 1962-03-12 | 1965-03-23 | American Cyanamid Co | Methods and compositions for rendering textile materials soft, germ resistant and antistatic |
US3951841A (en) * | 1972-06-08 | 1976-04-20 | Discwasher Inc. | Phonograph record cleaning composition |
US4547307A (en) * | 1981-09-17 | 1985-10-15 | Udo Hoppe | Cake of soap with deodorizing action |
WO2005044965A1 (en) * | 2003-11-10 | 2005-05-19 | Schwarzwälder Marketing Gmbh & Co. | Use of a solution comprising at least one nonionic surfactant |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2303932A (en) * | 1940-03-02 | 1942-12-01 | Bruno T Guild | Personal cleaning composition |
US2484784A (en) * | 1945-07-17 | 1949-10-11 | Allied Lab Inc | Bactericidal compositions |
GB761269A (en) * | 1953-04-24 | 1956-11-14 | American Cyanamid Co | Improvements in or relating to antiseptic detergent compositions and process of making the same |
US2865859A (en) * | 1956-11-09 | 1958-12-23 | Irwin I Lubowe | Solubilizing of mineral, vegetable, animal oils for cosmetic, pharmaceutical and industrial purposes |
US2880138A (en) * | 1956-12-24 | 1959-03-31 | Upjohn Co | Anti-inflammatory steroid solutions |
US2880130A (en) * | 1956-12-24 | 1959-03-31 | Upjohn Co | Anti-inflammatory steroid solutions |
US2942008A (en) * | 1956-12-10 | 1960-06-21 | Irwin I Lubowe | Solubilizing of mineral, vegetable, and animal oils for cosmetic, pharmaceutical, and industrial purposes |
US2961375A (en) * | 1957-08-27 | 1960-11-22 | Charles G Shaw | Nontoxic fungicidal preparations |
US2968628A (en) * | 1958-10-17 | 1961-01-17 | Shulton Inc | Propellant composition |
US2975099A (en) * | 1958-06-25 | 1961-03-14 | Upjohn Co | Polyethylene glycol suppository bases |
US2979410A (en) * | 1957-05-13 | 1961-04-11 | Tee Pak Inc | Food package and packaging film therefor |
US3029188A (en) * | 1958-02-20 | 1962-04-10 | Olin Mathieson | Gelatin adhesive pharmaceutical preparations |
-
1958
- 1958-03-26 US US723942A patent/US3069358A/en not_active Expired - Lifetime
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2303932A (en) * | 1940-03-02 | 1942-12-01 | Bruno T Guild | Personal cleaning composition |
US2484784A (en) * | 1945-07-17 | 1949-10-11 | Allied Lab Inc | Bactericidal compositions |
GB761269A (en) * | 1953-04-24 | 1956-11-14 | American Cyanamid Co | Improvements in or relating to antiseptic detergent compositions and process of making the same |
US2865859A (en) * | 1956-11-09 | 1958-12-23 | Irwin I Lubowe | Solubilizing of mineral, vegetable, animal oils for cosmetic, pharmaceutical and industrial purposes |
US2942008A (en) * | 1956-12-10 | 1960-06-21 | Irwin I Lubowe | Solubilizing of mineral, vegetable, and animal oils for cosmetic, pharmaceutical, and industrial purposes |
US2880138A (en) * | 1956-12-24 | 1959-03-31 | Upjohn Co | Anti-inflammatory steroid solutions |
US2880130A (en) * | 1956-12-24 | 1959-03-31 | Upjohn Co | Anti-inflammatory steroid solutions |
US2979410A (en) * | 1957-05-13 | 1961-04-11 | Tee Pak Inc | Food package and packaging film therefor |
US2961375A (en) * | 1957-08-27 | 1960-11-22 | Charles G Shaw | Nontoxic fungicidal preparations |
US3029188A (en) * | 1958-02-20 | 1962-04-10 | Olin Mathieson | Gelatin adhesive pharmaceutical preparations |
US2975099A (en) * | 1958-06-25 | 1961-03-14 | Upjohn Co | Polyethylene glycol suppository bases |
US2968628A (en) * | 1958-10-17 | 1961-01-17 | Shulton Inc | Propellant composition |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3174905A (en) * | 1962-03-12 | 1965-03-23 | American Cyanamid Co | Methods and compositions for rendering textile materials soft, germ resistant and antistatic |
US3951841A (en) * | 1972-06-08 | 1976-04-20 | Discwasher Inc. | Phonograph record cleaning composition |
US4547307A (en) * | 1981-09-17 | 1985-10-15 | Udo Hoppe | Cake of soap with deodorizing action |
WO2005044965A1 (en) * | 2003-11-10 | 2005-05-19 | Schwarzwälder Marketing Gmbh & Co. | Use of a solution comprising at least one nonionic surfactant |
US20070093405A1 (en) * | 2003-11-10 | 2007-04-26 | Ursula Maier | Use of a solution comprising at least one nonionic surfactant |
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