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Publication numberUS3899616 A
Publication typeGrant
Publication dateAug 12, 1975
Filing dateNov 9, 1973
Priority dateNov 9, 1973
Publication numberUS 3899616 A, US 3899616A, US-A-3899616, US3899616 A, US3899616A
InventorsSimonelli Frank A
Original AssigneeSimonelli Frank A
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Fungistatic fabric treatment
US 3899616 A
Abstract
A treatment for fabrics to provide fungistatic and fungicidal properties wherein the active ingredient in the treatment solution is undecylenic acid (CH2=CH(CH2)8COOH). The undecylenic acid is contained in an aqueous solution containing an emulsifier, laundry perfume, and zinc silicofluoride, and is used in the final rinse of a washing cycle.
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Description  (OCR text may contain errors)

United States Patent 1191 Simonelli [451 Aug. 12, 1975 FUNGISTATIC FABRIC TREATMENT [76] Inventor: Frank A. Simonelli, 2731 1ronwood Dr., Springfield, Ohio 45504 [22] Filed: Nov. 9, 1973 1 1211 Appl. No.: 414,350

[52] US. Cl. 427/242; 427/394; 427/346; 427/430 [51] Int. C1. A61L 13/00; DO6M 13/02 [58] Field of Search ..117/138.5, 139.5 CQ, 117/139.5 F. 47

[56] References Cited UNITED STATES PATENTS 2,689,809 9/1954 Fessler 117/138.5 2,885,319 5/1959 Ligett et a]. 117/138.5 X 3,033,704 5/1962 Sherrill et a1. 117/47 3,193,505 7/1965 Blomfield 252/106 X 3,200,035 8/1965 Martin et a1. 1l7/138.5 X 3,329,609 7/1967 Blomfield 252/8.8 3,432,341 3/1969 Berenson et a1. 117/138.5 3,498,829 3/1970 Lifland et a1. 117/138.5

3,555,159 1/1971 Feldman 252/8.6 X 3,729,422 4/1973 bozo 117/138.5 X 3,764,531 10/1973 Eckert et a1. 117/139.5 X

Primary Exam iherCameron K. Weiffenbach Assistant ExaminerRa1ph E. Varndell Attorney, Agengor Firm-Biebe1, French & Bugg 57 ABSTRACT A treatment for fabrics to provide fungistatic and fungicidal properties wherein the active ingredient in the treatment solution is undecylenic acid (CH CH(C1-1 COOH). The undecylenic acid is contained in an aqueous solution containing an emulsifier, laundry perfume, and zinc silicofluoride, and is used in the final rinse of a washing cycle.

4-1C1aims, No Drawings l FUNGISTATIC FABRIC TREATMENT I BACKGROUND OF THE INVENTION This invention relates to a method of treating fabrics to provide fungistatic and fungicidal protection. The preferred treatment is with a solution of undecylenic acid.

In recent years, increased attention has been given to the development of textile finishes and rinses. These are intended to reduce the number of microorganisms residing on the material whereby the treated materials may be used with less danger from harmful bacteria. Such finishes when applied to articles of clothing and other articles such as linen are helpful in preventing the development of mildew, rot and odors.

Articles subject to good laundering procedures will be generally bacteria-free, as well as fungus-free. If protected from contamination, they will remain so until used. However, if not protected prior to use, the articles may, and probably will, become contaminated with bacteria and/or fungus which is either air-borne or transmitted by contact with personnel handling these articles. Also, the growth of fungus in areas of high humidity is an unceasing problem.

Various textile purifying finishes containing antibacterial substances such as hexachlorophene, tetrachlorophene, quaternary ammonium compounds such as dimethylbenzyl ammonium chloride, metal complexes of mercury, copper and silver, organic compounds and other have been used. Aromatic mercury compounds are also known as good bacteriostatic and fungistatic compounds.

Still other textile treatments are disclosed in the patent literature. For example, U.S. Pat. No. 3,240,710 is directed to a washing compound having antibacterial properties. This compound includes lauryl-pyridinium 2-(5-chlorobenzothiazyl) sulfide and halogenated .salicylanilides in a built soap.

U.S. Pat. No. 3,058,013 also discloses a germicidal compound for treating textiles. The treatment solution of this patent includes an organic mercury compound. U.S. Pat. No. 3,432,341 shows yet another method of protecting fabrics from bacterial and fungal attack. The

compounds used here are alkylenebis (triphenylphosphonium) salts. It is disclosed that this germicide treatstatic compounds have been and are used to treat textiles, no one, as far as is known, has used undecylenic acid for that purpose, although the desirability of doing sodias long been recognized. Undecylenic acid is one of the most active acids having fungistatic and fungicidal action. Wyss et al., Arch. Biochem., 7: 415-425, 1945; Golden et al., J, Am. Pharm. Assoc., Sci. Ed. 36: 359-362, 1947. It is also a known bacteriostatic and bactericidal agent. Keeney et al., Bull. Johns Hopkins Hosp., 77: 437-440, 1945; Katsura, Tohokii J. Exptl. Med, 49: 357-364, 1948.

Coupled with the recognized effectiveness of undecylenic acid is the fact that it is safe and non-irritating, as well as being very inexpensive compared to most of the treatments mentioned above. The problem is that it is not readily water soluble and, thus, not suitable for application to fabrics during laundering. Thus, for example, Fessler in U.S. Pat. No. 2,689,809 found it necessary to use a water-soluble salt of undecylenic acid when using that germicide in treating articles.

SUMMARY OF THE INVENTION The invention is directed to the treating of fabrics with an aqueous solution containing undecylenic acid to provide bacteriostatic, bactericidal, fungistatic and fungicidal protection. The preferred treatment involves exposing the fabric to an aqueous solution of undecylenic acid CH =CH(CI-I COOH), emulsifier, perfume, etc., in the form of a final rinse during the normal rinse cycle of a normal washing method, spin-drying the fabric to remove excess undecylenic acid rinse, and, finally, drying the fabric.

Stock concentrations containing at least 0.1% (0.100 grams/ ml.) of undecylenic acid are used in the final rinse cycle of the washing machine. The concentrate is added to the rinse water at the approximate rate of 100 ml per gallon of rinse water. After drying the treated fabric contains 0.05 0.1% by weight of undecylenic acid. This is an effective inhibitory concentration.

The treatment of the present invention has unlimited possibilities in geographic areas of high humidity and high mildew incidence since it prevents the growth of the fungi which thrives under such conditions. Thus, the invention is particularly applicable to linen supply laundries, which supply linens to restaurants and other establishments, and to institutions, such as hospitals,

etc., which have their own laundries or to any other fabric treating or laundering facility which needs to supply sanitary, bacteria resistant goods. It is safe, effective, and inexpensive.

In the past, while many solutions and methods of treating fabrics to provide germicidal protection have,

been known, none has, as yet, used an aqueous solution of undecylenic acid as the active ingredient, to provide bacteriostatic, bactericidal, fungistatic and fungicidal protection treatment.

It is, therefore, an object of this invention to provide a novel method of treating fabrics to provide fungistatic, fungicidal, bacteriostatic and bactericidal protection using an aqueous undecylenic acid solution.

It is a further object of this invention to provide an undecylenic acid solution which can be used in the novel method of this invention to treat fabrics to provide fungistatic, fungicidal, bacteriostatic and bactericidal protection.

Other objects and advantages of the present invention will be apparent from the following description and the appended claims.

DESCRIPTION OF THE PREFERRED EMBODIMENT In general, this invention relates to the discovery that by applying a final rinse of an aqueous undecylenic acid solution to fabrics, when the fabrics are dried, they are IO-undecenoic acid;

provided with fungistatic, fungicidal, bacteriostatic and bactericidal protection.

The preferred method of treatment consists of the following steps:

. a. forming a concentrate of undecylenic emulsifier, and other possible ingredients,

b. diluting the concentrate with water to form an aqueous undecylenic acid solution, which is applied as a final rinse in a normal final rinse cycle of a normal washing method, as in a washing machine,

c. rinsing the fabric with the aqueous undecylenic acid solution by agitating the fabric and the solution together for about 10 minutes,

, 'd. spinning dry to remove the excess solution out of the fabric, and

e. drying-the fabric.

As an example, 100 milliliters of stock concentrate was prepared as follows:

acid, an

undecylenic acid (98%) emulsifiers laundry perfume zinc silicofluoride 1% (1.0 gram/ 100 ml.) water remainder While this is one preferred concentrate, it has been found that the fungicidal action of the undecylenic acid in treated fabric is with stock. concentrates having above 0.1% (0.100 grams/100 ml.) undecylenic acid. Solutions made from concentrates having above that amount of undecylenic acid are effective. Thus, the preferred range of ingredients in the concentrate is 0.1 5% undecylenic acid, 0.1 5% emulsifier, 1% zinc silicofluoride, a trace of laundry perfume, if any is added at all, and the rest water.

' The w orking solution,'i.e the undecylenic acid solution which is the final rinse which is applied to the fabric, may consist of 100 milliliters (ml.) of the stock concentrate diluted with one gallon (approximately 4 liters 5% (5.0 grams/100 ml.) 5% (5.0 ml/lOO ml.) trace of wa t er This'g'ives a rinse water solution having the following concentrations:

undecylenic acid 125% zinc silicofluoride .025%

trace laundry perfume Since undecylenic acid is water insoluble it is difficult to apply' to a-fabric from an aqueous solution. In order to do so it has been found necessary to emulsify it in order to form an aqueous solution. Suitable emulsifiers are polysorbate 80 (sold as TWEEN 80), which is a mixture of polyoxyethylene ethers of mixed partial oleic esters of sorbitol anhydrides such as polyoxyethylene sorbitan mono-oleate and sorethytan mono-oleate, or TERGlTOL NONlONlC 15-S-9 (sold by Union Carbide), which is an ether of polyethylene glycol. These are the preferred emulsifiers although others may be employed. They are preferred because they are biodegradable, effectively utilized in almost all textile wet finishing processes, and are nontoxic (either as a pri- A cationic-type fabric softener may be added, if desired, to the final rinse water with the undecylenic acid without affecting the fungicidal properties of the rinse solution.

Textile (cloth) fabrics were treated according to the method of the invention. The resultant fabrics con tained by weight of fabric 0.05 0.1% undecylenic acid. These fabrics were then tested to determine their resistance to mildew and rot when so treated, i.e., to evaluate their fungistatic and fungicidal protection. The tests were done according to the recommendations outlined in the technical manual of the American Association of Textile Chemists and Colorists, Part Ill, AATCC, Test Methods, 82, Lowell, Mass, 1959. In addition to the procedures described by AATCC, the treated cloth samples were subjected to fungal broth cultures and varying temperatures and humidity.

The biological testing consisted of inoculating fabric (cloth) samples, treated with undecylenic acid, with test fungi (l) Chaetomium globosun (ATCC 6205 on AATCC mineral salts agar) and (2) Aspergillus niger (ATCC 6275-AATCC mineral salts agar plus dextrose). In addition to the procedures described by the AATCC, a duplicate set up was tested using AATCC broth with test fungi (with high spore count).

All the samples were incubated for twenty-one days in the following environments:

a. Room temperatures (27-20C) with a relative humidity of 50%;

b. Human body temperature (37C) with relative humidity of 50 to 90%;

0. High temperature (C) with a relative humidity The treated cloth samples were subsequently treated at weekly intervals with nutrient broth to stimulate spore germination.

' The result was that the undecylenic acid treated cloth samples, as tested, demonstrated fungistatic and fungicidal protection showing little or no growth in the contact area. The minimum inhibitory concentrations of undecylenic acid in the biological testing (both agar andbroth cultures and in fabrics) was found to be 0.05 to 0.1%.

The method and solution of the present invention may be used in linen supply plants, which do laundry for restaurants and other establishments, as well as institutions, i.e., hospitals, etc., which have their own laundries. It is these types of organizations which must stockpile linens, etc., and yet when they must be used, the linens, etc., must be of acceptable appearance and cleanliness. The method is very useful in areas of high mildew incidence.

The principles of the present invention may be used in other instances where fungistatic and fungicidal protection is desired, such as e.g., treating paper fibers,

leather in plastic coating compositions, soaps, cosmetics, agricultural sprays, etc. The various other uses of the present invention will be readily apparent to those skilled in the art.

While the method and solution described constitute preferred embodiments of the present invention, it is to be understood that the invention is not limited to the quantities and steps described and that changes may be made in either without departing from the scope of the invention which is defined in the appended claims.

What is claimed is:

l. A method of treating fabrics to provide bacteriostatic, bactericidal, fungistatic and fungicidal protection comprising the following steps:

a. mixing the following to form a concentrate consisting essentially of undecylenic acid .1 5% emulsifiers .1 5% laundry perfume trace zinc silicofluoride .0 1% water remainder e. continuing to rinse the fabric with the mixture by agitating the fabric in the mixture for a period of about ten minutes as a part of said rinse cycle,

f. spinning dry the fabric to remove the excess rinse mixture, and

g. drying said fabric.

2. A method of treating fabrics as set forthin claim 1 wherein said emulsifier is selected from the group consisting of polysorbate and polyethylene glycol ethers.

3. A method as set forth in claim 2 wherein the rinse solution contains 0.125% undecylenic acid, 0.125% emulsifier, 0.25% zinc silicofluoride, and a trace of laundry perfume.

4. A cloth treated by the process of claim 1 so as to be free from bacterial and fungal attack, said cloth containing 0.05 0.1% residual undecylenic acid after treatment.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2689809 *Oct 8, 1951Sep 21, 1954Permachem CorpSelf-sterilizing article and its preparation
US2885319 *Dec 17, 1953May 5, 1959Pittsburgh Coke And Chemical CN-phenylmaleamic acid esters as fungicides
US3033704 *May 19, 1959May 8, 1962Armour & CoRendering fabric anti-static, soft, and microorganisms resistant
US3193505 *Sep 20, 1961Jul 6, 1965Wyandotte Chemicals CorpAntimicrobial laundry sour composition
US3200035 *Jun 4, 1962Aug 10, 1965Ciba LtdTreatment of synthetic products, especially synthetic fibers
US3329609 *Mar 22, 1965Jul 4, 1967Wyandotte Chemicals CorpCompositions containing quaternary ammonium salts
US3432341 *Jul 27, 1967Mar 11, 1969American Cyanamid CoProtecting fabrics with a bacteriotoxic-fungitoxic application of alpha,omega-alkylenebis (triphenylphosphonium salt)
US3498829 *Oct 19, 1967Mar 3, 1970Kendall & CoMethod for producing a bacteriostatic finish on synthetic fabrics
US3555159 *Mar 14, 1967Jan 12, 1971Baxter Laboratories IncAntimicrobial composition and method of use
US3729422 *Mar 22, 1971Apr 24, 1973Basf Wyandotte CorpMildewstatic laundry sour basf
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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US5976460 *Dec 24, 1996Nov 2, 1999Elf Atochem S.A.Use of a deodorizer based on undecylenic acid or on derivatives of the said acid to deodorize papers, cardboards and nonwovens
US7939686Feb 25, 2004May 10, 2011Supreme CorporationImmersing in aqueous bath, separation, drying; quaternized cationic copolymer of octadecylaminodimethyltrihydroxysilylpropyl ammonium chloride and chloropropyltrihydroxysilane
EP0781562A2 *Dec 24, 1996Jul 2, 1997Elf Atochem S.A.The use of a deodorant based on undecylenic acid or its derivatives for the deodorization of paper, cardboard or non-woven material
EP1718788A2 *Feb 25, 2005Nov 8, 2006Supreme Elastic CorporationMethod for providing antimicrobial composite yarns, composite fabrics and articles made therefrom
WO2000051560A1 *Mar 1, 2000Sep 8, 2000Harry HayesFragrance and flavor compositions containing odor neutralizing agents
Classifications
U.S. Classification427/242, 427/346, 427/430.1, 427/394
International ClassificationD06M16/00, C11D1/04, C11D1/02, A61L9/01
Cooperative ClassificationC11D1/04, A61L9/01, D06M16/00
European ClassificationC11D1/04, A61L9/01, D06M16/00