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Publication numberUS3770373 A
Publication typeGrant
Publication dateNov 6, 1973
Filing dateMay 10, 1972
Priority dateAug 22, 1969
Also published asUS3697220
Publication numberUS 3770373 A, US 3770373A, US-A-3770373, US3770373 A, US3770373A
InventorsG Schwartz
Original AssigneeSchwartz Chem Co Inc
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Drycleaning deodorizing and disinfecting compositions and processes
US 3770373 A
Abstract  available in
Images(7)
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Claims  available in
Description  (OCR text may contain errors)

United States Patent 1 Schwartz *Nov. 6, 1973 DR YCLEANING DEODORIZING AND DISINFECTING- COMPOSITIONS AND PROCESSES Inventor: George C. Schwartz, Casselberry,

Fla.

Schwartz Chemical Company, Incorporated, Casselberry, Fla.

Assignee:

Notice: The portion of the term of this patent subsequent to Oct. 10, 1989, has been disclaimed.

Filed: May 10, 1972 Appl. No.: 252,095

Related US. Application Data Continuation-impart of Ser. No. 52,764, July 6, 1970, Pat. No. 3,697,220, which is a continuation-in-part of Ser. No. 852,491, Aug. 22, 1969, abandoned.

US. Cl 8/142, 117/138.5, 252/106,

424/226, 424/249 Int. Cl D06l 1/00 Field of Search 8/142; 252/106;

References Cited UNITED STATES PATENTS 3,697,220 10/1972 Schwartz 8/142 3,228,829 1/1966 Wolf et a1. 424/249 Primary Examiner-Mayer Weinblatt Assistant Examiner-Harris A. Pitlick Att0rneyMarcus B. Finnegan et al.

[ 57] ABSTRACT 23 Claims, No Drawings DRYCLEAN I NG DEODORIZING AND DISINFECTING COMPOSITIONS AND PROCESSES This application is a continuation-in-part of my copending application Ser. No. 52,764, filed July 6, 1970 now U.S. Pat. No. 3,697,220, which application was a continuation-in-part of application Ser. No. 852,491, filed Aug. 22, 1969 and now abandoned.

This invention relates to the drycleaning of fabrics or textiles and more particularly to certain chemically disinfected textiles that contain a bacteria growth inhibitor and to certain drycleaning and disinfecting compositions and methods.

There is a false popular belief that the drycleaning of textiles or woven fabrics involves a germicidal process which is destructive of the vegetative forms of pathogenic or disease causing microorganisms. it is well established however, that such procedures have only limited antibacterial effects, (see Microbiology of Dry Cleaning, by Robert R. Banville and Ethel McNeil, Appl. Microbiol. l4:1-7. 1966) and that many bacteria carry through the drycleaning process on the fabrics or textiles and/or are redeposited on the fabrics and textiles during the cleaning procedures. Such carry through and redepositions are, of course, undesirable because there is the resultant spread ofdisease producing bacteria which, if destroyed during the drycleaning procedure, would be incapable of causing subsequent human infection.

The inventor is unaware of any commercialized dry cleaning procedure that simultaneously cleans and disinfects textiles or fabrics. On the other hand, it is known to fumigate textiles with formaldehyde vapors as a step separate and apart from'the cleaning step and as a means for disinfecting the textiles by the destruction of the pathogenic bacteria therein.

Procedures for simultaneously cleaning and disinfecting textiles have been proposed in the past but suffer from one or more disadvantages which have prevented their commercialization insofar as the' inventor is aware. For example, it is known to incorporate formaldehyde or formalin, as a disinfectant or germicide, in organic fat solvents that may be used in drycleaning procedures. The compositions, however, suffer the disadvantage that during the cleaning process, the formaldehyde imparts a pungent odor to the textile and which requires removal by a subsequent neutralization step. This added step of course, substantially increases the time and cost of cleaning and disinfecting the fabrics. The incorporation of other antimicrobial agents in the fat solvents suitable .for use in commerical drycleaning processes has also been proposed. Among the-problems which have confronted investigators in this field, however, is that of finding an antimicrobial agent which is compatible with the solvents and detergents used in commerical drycleaning procedures and which is also germicidally effective and economical to use in treating the textiles under the normal conditions which are encountered in modern commerical drycleaning establishments.

The inventor has discovered that l-(3-chloroallyl)- 3,5,7-triaza-l-azoniaadamantane chloride is not only compatible with the commerically employed organic fat solvents, such as perchloroethylene and stoddard solvent, and with the usual nonionic and anionic detergents that are employed in the commerical drycleaning procedures, but that the compound serves as an effective antimicrobial agent in system involving such fat solvents and detergents and is capable of accomplishing the disinfection of the textiles under the operating conditions which are normally encountered in commerical drycleaning plants.

The antimicrobial agent advocated for use herein is insoluble in such organic fat solvents as perchloroethylene and stoddard solvent, but has a high degree of solubility in water that amounts to better than 2.2 grams of the l-( 3-chloroallyl )-3,5 ,7-triazal azoniaadamantane chloride per gram of water. This has led to the discovery that the antimicrobial agent can be introduced as an additive to thecurrent day drycleaning compositions and will therein become soluble in the small amounts of water which normally enter the system with the textiles during the cleaning procedures. This introduced water becomes emulsified and colloidally dispersed by the synthetic detergents and consequently, the compositions of the invention are emulsions of the water in-oil type and wherein the antimicrobial agent is present in an aqueous solution that constitutes the dispersed phase of the emulsion while the organic fat solvent provides the continuous phase of the emulsion. Textiles which are contacted by the compositions of the invention, as by being immersed and agitated with the compositions in accord with conventionaldrycleaning procedures, and which are thereafter dried are not only cleaned and disinfected but have been found to thereafter inhibit bacterial growth as will be subsequently apparent.

A general object of the invention is to provide improvements in the field of drycleaning.

Yet another object of the invention is to provide drycleaning and disinfecting compositions which can be used for the drycleaning of textiles and woven fabrics in accord with conventional drycleaning techniques and without the need for modifying or changing the equipment used in the current commerical drycleaning procedures.

Yet another object of the invention is to provide a process for drycleaning and disinfecting fabrics or textiles and which can be carried out in commerical drycleaning equipment without the modification of such equipment or changes in the drycleaning techniques that are usually employed.

Yet a further object of the invention is to provide drycleaning solutions which contain an antimicrobial agent which without imparting odors to the textiles is capable of effectively disinfecting textiles that are cleaned in such solutions. f

Yet a further object of the invention is to provide drycleaning solutions which contains an antimicrobial agent which is capable of effectively disinfecting, sanitizing, and deodorizing textiles that are cleaned in such solutions.

Yet another object of the invention is to provide compositions for use in drycleaning and disinfecting textiles and which can be easily prepared and maintained by people which are basically unskilled in the formulation of chemical compositions and which can also be economically used for such purposes.

A further object of the invention is .to provide a drycleaning and disinfecting process which not only disinfects fabrics and other textiles subjected to the process but which imparts bacteria growth inhibiting properties to the textiles thus subjected to the process.

- chloroallyl )-3 ,5 ,7-triaza-1-azondiaadamantane Another object of the invention is to provide textiles which have bacteria growth inhibiting properties.

In accord with the invention, the textile drycleaning and disinfecting compositions are emulsions of the socalled water-in-oil type and comprise a liquid organic fat solvent that forms the medium or continuous phase of the emulsion, an aqueous solution of 1-(3- chloride which is colloidally dispersed in the fat solvent, and an emulsifier in amounts sufficient to provide a stable emulsion so that the antimicrobial agent containing dispersed phase will be brought into effective contact with textiles subjected to cleaning procedures involving the use of the compositions.

The fat solvent may be one or more of the liquid organic solvents that are suitable for drycleaning purposes, such as chlorinated lower aliphatic hydrocarbons, exemplified by perchloroethylene, carbontetrachloride, trichloroethylene, etc. and the aromatic and saturated aliphatic hydrocarbons such as stoddard solvent, benzene, benzol and the gasolines. In modern drycleaning plant practices stoddard solvent or perchloroethylene are by far the most widely used and preferred.

Information currently available indicates that emulsions which are suitable for the cleaning and disinfecting of textiles under commerical drycleaning plant practices should have at least 0.1 ounce (weight) of the additive present per one hundred gallons of the emulsion in order to effectively disinfect textiles which are cleaned in the compositions. Available information also indicates that the antimicrobial agent adheres to and impregnates the textiles during the cleaning procedures and is accordingly progressively removed from the emulsions with each batch of garments that are treated by the solutions. Accordingly, in plant practice the l-(3-chloroallyl)-3,5,7-triaza-l-azoniaadamantane chloride content of the emulsions is replenished periodically on the basis of the weight of the textiles treated in the emulsions and in this respect, it has been found that one hundred gallons of an emulsion which initially contains one ounce of the l -(3'chloroallyl)-3,5,7- triaza-l-azondiaadamantane chloride will effectively clean and disinfect nine hundred pounds. of garments before the concentration of the additive diminishes to an unacceptable level for satisfactory disinfection of the further treated textiles.

Insofar as the water content of the emulsions is concemed, the amount of water need be no more than enough to dissolve effective amounts of the antimicrobial agent. In this respect, the weight of water in the emulsion should preferably exceed 45 percent of the weight of the l-( 3-chloroallyl)-3,5,7-triaza-lazoniaadamantane chloride content of the emulsion in order to insure complete solution of the antimicrobial agent and its dispersement throughout the emusion. ln commerical drycleaning plant practices the drycleaning compositions usually contain from one pint to as much as a quart of water per hundred gallons of the cleaning solution because of the water content of the garments that are charged to the solutions. The amount, of course, varies in accord with existing humidity conditions but it has been found that the amount of water which exists in such compositions is more than adequate to dissolve the amounts of the antimicrobial agent and which would normally be added during the drycleaning procedures.

Insofar as the emulsifier in'the composition is'concemed, the emulsifier can be any one or more of the soaps or synthetic detergents that are useful as cleaning aids or boosters in commerical drycleaning solutions and which, among other things, serve to dispose the water content of such solutions and provide stable emulsions. Examples of suitable emulsion forming surfactants of the nonionic type are the products formed by condensing the alkalene oxides, for example, with the high molecular weight fatty alcohols, amines, carboxylic acids, amides and alkylphenols to mention a few. Examples of the emulsion forming surfactants of the anionic type are the soaps, fatty alcohol sulfates, alkane sulfonates, alkylaryl sulfonates, succinic acid ester sulfonates, and fatty acid ester sulfonates to mention a few. The surfactants which serve as the emulsifler are used in amounts which are sufficient to provide a stable emulsion and are preferably employed in small amounts between about 0.5 and 2.0 percent by weight of the emulsion.

In carrying out the process aspects of the invention, the textiles are immersed and agitated in the drycleaning compositions advocated herein so as to thoroughly contact the textile with the drycleaning and disinfecting composition and the contact between the composition and the textiles is maintained for a period of time which is sufficient to destroy the vegetative forms of the pathogenic microorganism introduced with the textiles. The contact time or period will, of course, vary in accord-with the type and strain of bacteria adhering to or otherwise incorporated with the textile, but even with the more resistant strains of bacteria, a contact time of fifteen minutes under the usual drycleaning conditions which exist in commerical drycleaning'plant practices has been found to provide satisfactory garment disinfection. As will be subsequently seen, compositions contemplated herein have shown one hundred percent germicidal activity against Salmonella Choleraesuis where contact has been maintained for fifteen minutes and similar activity against strains of Staphylococcus Aureus where contact has been maintained for-five minutes. Following .the contact with the compositions, the textiles need only be dried in the usual manner.

Textiles treated in accord with the process are impregnated with bacteria growth inhibiting amounts of the antimicrobial agent and current information indicated that the growth of vegetative forms'of such bacteria as staphylococcus aureus may be inhibited in fabrics or garments containing residual amounts in excess of about 0.5 grams of the antimicrobial agent per pound of fabric.

Textiles treated in accordance with the present invention are not only cleaned and disinfected, they are also deodorized. Conventional drycleaning is effective to deodorize textiles to a certain degree, but the degree ,of deodorization is not as great as is desired. Certain odors, such as those of domesticaminals, particularly cats, are only poorly removed by conventional drycleaning. The technique of the present invention is effective to deodorize textiles and is particularly effective in removing diflicult to remove odors, such as the odor of cats. The compositions of the present invention are also effective to destroy urine, perspiration, vomit and personal illness odors from garments without contributing an odor of its own.

It has also been discovered that l-(3-chloroallyl)- 3,5,7-triaza-l-azoniaadamantane chloride is effective torcmove smoke odors. Smoke odors may be removed from textiles only with great difficulty, particularly when the textiles have been subjected to heavy s'moke such as that resulting from a fire. Normal drycleaning is not effective to remove such odors. When it is desired to remove heavy smoke odors from textiles, the concentration, of l-(3-chloroallyl)-3,5,7-triaza-lazoniaadamantane chloride in the drycleaning solvent should be increased over the amount needed merely to disinfect. Smoke odors are effectively removed by drycleaning if the chloride is present in an amount exceeding 12 ounces perlOO gallons of the drycleaning solvent.

The preferred method of removing smoke odors from textiles may be accomplished with a conventional drycleaning machine. Such machines generally employ about 60 to 100 gallons of solvent, which solvent is maintained in a storage tank and circulated through a filtration system into the cleaning apparatus. To removesmoke odors, the fabrics are placed in the drycleaning machine and the machine is run in a conventional manner for about minutes to remove general soil and stains. The filter is then turned off so that solvent is no longer circulated through the system. About 2 to 3 ounces of l-( 3-chloroallyl)-3,5,7-triaza-lazoniaadamantane chloride, dissolved in a small amount of water (about 2 to 6 ounces), is added directly to the solvent retained in the cleaning apparatus (typically about 10 to gallons). The machine is then operated for about 5 to 10 minutes, without circulation of solvent through the system, after which time the solvent retained in the cleaning apparatus is dumped, the solvent retained by the textiles is extracted, and the textiles are tumble dried. The solvent used to remove the smoke odors may be subsequently distilled and returned to the system. Of course, the smoke removal procedure is effective to disinfect the textile materials.

Dispersions of at least 12 ounces of l-(3-chloroallyl)- 3,5,7-triaza-l-azoniaadamantane chloride in 100 gallons of drycleaning solvent are also effective to remove smoke odors from materials other than textiles. Smoke odors, such as those resulting from a fire in a building, can be removed from walls, furniture, etc. by washing the item with the dispersion. No special equipment is required; the smoke damaged item may be merely swabbed down with the dispersion and allowed to dry.

EXAMPLE l 100 gallons of a basic commerical drycleaning solvent essentially consisting of perchloroethylene, a 1 re percent (wt) charge of detergent material, and a small amount (about 1 quart) of water emulsified therein,

No. 209) grown in a nutrient broth as specified in Official Methods of Analysis, A. O. A. C.

1 cc. of nutrient broth containing 100 X 10 organisms per cc. was absorbed ineach of two 1 square inch cotton toweling swatches which were then air dried for 12 hours. 'One of the dried swatches was agita-ted for 5 minutes in 50 cc. of the base solvent while the other swatch was agitated for an identical period in 50 cc. of the disinfecting composition after the composition had been previously used on a commerical scale to clean and disinfect 200 lbs. of garments. After a 1 hour drying time, the swatches were separately pulverized in a blender and diluted to 1 liter with sterile water. 0.01 cc. samples of each diluted solution were then streaked onto nutrient agar plates in triplicate, and the plates were then incubated at 37c and examined after 24 hours, 48 hours and 72 hours. The colonies were counted at each examination with the results shown below:

COLONlES Incubation Period 24 hr. 48 hr. 72 hr. Base Solvent Control Plate 1 16.0 17.0" l7.2* Control plate 2 20.0 20.8 21.0 Control Plate 3 l8.0* l8.8 l9.0" Disinfectant Composition Test Plate 1 0 0 0 Test Plate 2 0 0 0 Test Plate 3 0 0 0 times 10 EXAMPLE ll 1 ounce of l-( 3-chloroallyl )-3 ,5 ,7-triazal azoniaadamantane chloride was added to gallons of a basic commerical drycleaning solvent which was in use in a 100 gallon commerical size drycleaning plant and which essentially consisted of perchloroethylene, a l (wt) charge of detergent material, and a small amount (about 1 quart) of water. emulsified therein to provide a drycleaning and disinfecting composition withrespect to test cultures of staphylococcus aureus and salmonella choleraesuis grown in nutrient broth.

The official A. O. A. C. use-dilution method, moditied to utilize 1 square inch cotton toweling swatch as carriers was used, with 30 swatches being used for each test and 10 swatches for each control. Procedurally 1 cc. of broth, containing 100 X 10 organisms per cc. was placed on each swatch and the swatches air dried for 24 hours. The swatches used in the tests were agitated for 5 minutes, 10 minutes and 15 minutes in respective 200 cc. samples of the drycleaning and disinfecting composition after the composition had been previously used on a commerical scale to clean and disinfect 460 pounds of garments, whereas, the swatches used in the control runs were agitated for like periods in 200 cc. samples of the basic solvent,

All swatches were aseptically transferred to a vacuum-desiccator and after 1 hour of desiccation transferred to nutrient broth tubes and incubated at 37C, for

48 hours. Each tube was then examined for growth with the results shown below.

Test Control Runs (30 Tubes) (10 Tubes) Staphylococcus Aureus Contaminated Swatches 5 min. Agitation 30 neg. 10 plus Salmonella choleraesuis Contaminated Swatches 5 min. agitation 21 neg.9 plus l0 plus 10 min. agitation 28 neg-2 plus 10 plus 15 min; agitation 30 neg. 10 plus neg.=no growth plus=growth EXAMPLE lll To determine the bacterial growth inhibiting properties of textiles cleaned and disinfected in drycleaning and disinfecting compositions containing l-(3- chloroallyl )-3 ,5 ,7 -triazal -azoniaadamantane chloride and to' determine thereplenishme'nt cycle for compositions initially-containinglounce of l (3-chloroallyl)- 3,5,7-triaza-l-azoniaadamantane chloride per 100 gallons of composition, two runs were made in a 100 gallon commerical size drycleaning plant where the equipment was successively charged with weighed and usually approximately 20 lbs. of garments, that were agitated in the equipment for 20 minutes with the solvent composition before being removed and dried. The composition at the beginning of each run consisted essentially of perchloroethylene, a small amount (about 1 quart) of water, 1 7% percent (wt) of detergent material, and 1 ounce of l-(3-chloroallyl)-3,5,7-triaza-1- azoniaadamantane chloride.

The method used is in Federal Specification No. UU- P-5l0, Paragraphs 4.4.2.1-4.4.2.4 and the test culture was staphylococcus aureus (F. D. A. No. 209), grown in nutrient broth as specified in Official Methods of Analysis, A. O. A. C.

Procedurally, and at selected intervals during each run, 1 square inch test swatches of cotton toweling were laundered in the emulsified drycleaning and disinfecting composition along with other garments. After air drying, each test swatch was placed on the surface of a pour plate that had been freshly prepared and inoculated with 0.1 cc. of the test culture. The specimens were then allowed to incubate at 37c for 24 hours before the zone of inhibition, as measured in millimeters from the edge of the swatch to the edge of the bacterial growth, was recorded, the results being shown below and wherein it is evident that the compositions have a satisfactorily long life before the need for replenishment of the l-(3-chloroallyl)-3,5,7-triaza-lazoniaadamantane chloride arises and that the swatches have bacteria growth inhibiting properties.

Total Garment Poundage Preceding Test Switch EXAMPLE IV Similar results may be secured by substituting stoddard solvent for perchloroethylene in the prior examples.

While the above examples have been set forth as illustrative of the invention, it should be understood that it is intended herein to cover all such modifications as fall within the true spirit and scope of this invention.

What is claimed as new and what it is desired to secure by Letters Patent of the United States is:

1. An emulsion of the water-in-oil type for use in drycleaning, deodorizing, and disinfecting consisting essentially of:

A. an organic drycleaning solvent;

B. an emulsifying agent in an amount sufficient to stabilize the emulsion; and

C. an aqueous solution of l-(3-chloroallyl)-3,5,7-

triaza-l-azoniaadamantane chloride colloidally dispersed in said drycleaning solvent, said aqueous solution being present in an amount of at least one pint per 1 OO'gallOns of the emulsion and said chloride being present in an amount exceeding 12 ounces per gallons of the emulsion.

2. The emulsion of claim 1 where the solvent is stoddard solvent.

3. The emulsion of claim 1 where the solvent is perchloroethylene.

4. An emulsion for use in drycleaning and disinfecting, deodorizing in accord with claim 1 where said emulsifying agent consists essentially of an anionic surfactant.

5. An emulsion for use in drycleaning and disinfecting, deodorizing in accord with claim 1 where said emulsifying agent consists essentially of a nonionic surfactant.

6. A method for simultaneously drycleaning, deodorizing, and disinfecting a textile comprising:

A. contacting an odoriferous textile for a period of time in excess of five minutes with a stable emulsion consisting essentially of:

1. an organic drycleaning solvent;

2. an emulsifying agent in an amount sufficient to stabilize the emulsion; and

3. an aqueous solution of l-(3-chloroallyl)-3,5,7-

triaza-l-azoniaadamantane chloride colloidally dispersed in the solvent, said emulsion containing about one pint to one quart of water and said chloride being present in the emulsion in an amount exceeding 0.1 ounce per 100 gallons of the emulsion;

B. thereafter removing the textile from the emulsion;

and

C. drying the textile.

7. A method in accord with claim 6 where the solvent is stoddard solvent.

8. A method in accord with claim 6 where the solvent is perchloroethylene.

9. A method for simultaneously drycleaning, deodorizing and disinfecting textiles in accord with claim 6 where said emulsifying agent consists essentially of an anionic surfactant.

10. A method for simultaneously drycleaning, deodorizing and disinfecting textiles in accord with claim 6 where said emulsifying agent consists essentially of a nonionic surfactant.

11. A process effective to simultaneously dryclean, disinfect, and remove smoke odors from a textile comprising:

A. contacting the textile for at least 5 minutes with a stable emulsion of the water-in-oil type consisting essentially of:

1. an organic drycleaning solvent;

2. an emulsifying agent in an amount sufficient to stabilize the emulsion; and

3. an aqueous solution of l-(3-chloroaJlyl)-3,5,7-

triaza-l-azoniaadamantane chloride colloidally dispersed in said solvent, said aqueous solution being present in an amount of at least one pint per 100 gallons of said emulsion, and said chlo- 1 ride being present in the emulsion in an amount exceeding 12 ounces per 100 gallons of said solvent;

B. thereafter removing the textile from the emulsion;

and C. drying the textile. 12. A method in accord with claim 11 where the solvent is stoddard solvent.

13. A method in accord with claim 11 where the solvent is pe'rchloroethylene.

14. Theemulsion of claim 1, in which said aqueous solution contains an amount of water exceeding 45 percent by weight of said chloride.

15. The emulsion of claim 1, in which said aqueous solution is present in an amount of no more than one quart per 100 gallons of emulsion.

16. The method of claim 6, in which said emulsifying agent consists essentially of a mixture of anionic and nonionic surfactants.

17. The method of claim 6, in which said odoriferous textile has the odor of cats.

18. The method of claim 6, in which said chloride is present in said solution in an amount exceeding 12 ounces per 100 gallons of said emulsion.

19. The method of claim 6, in which said aqueous solution contains an amount of water exceeding 45 percent by weight of said chloride.

20. The method of claim 6, in which said emulsifying agent consists essentially of a mixture of anionic and nonionic surfactants.

21. The process of claim 11, in which said aqueous solution contains an amount of water exceeding 45% by weight of chloride.

22. The process of claim 11, in which said aqueous solution is present in an amount of no more than one quart per gallons of said emulsion.

23. The process of claim 11, in which said emulsifying agent consists essentially of a mixture of anionic and nonionic surfactants.

f UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Dated November 6, 1973 Patent No. 3, 770, 373

Inventor( (leorge Cifichwartz It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as' shown below:

Claim 4 should read as follows -An emulsion for use in drycleaning, deodorizing, and disinfecting in v accordwith claim 1 Where said emulsifying agent consists essentially of an anionic surfactant.

Claim 5 should read as follows --An emulsion for use in I drycleaning, deodorizing, and disinfecting in I accord'with claim l'where said emulsifying agent consists essentially; of a nonionic surfactant. I

Claim 21, Column 10, line 9, after 'of" insert -sai d-.

Signed and sealed this 30th day of April 197M.

(SEAL) Attest:

FEM-{ARE E-LITLETCHERJR. 0 MARSHALL DAliiI Attesting Officer Commissioner of Patents uscoMM-oc wen-Pug fi U.S. GOVERNMENT PRINT NG OFFICE; IQ GI Q -Gl-la FORM PO-1050(10-69)

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US3228829 *Nov 4, 1963Jan 11, 1966Dow Chemical CoPreservation of aqueous dispersions
US3697220 *Jul 6, 1970Oct 10, 1972Schwartz Chem Co IncBacteria growth inhibiting textiles and dry cleaning and disinfecting compositions and processes
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4142985 *Jan 23, 1978Mar 6, 1979Louderback Allan LeeMethod of formulating a germicidal soap
US5547476 *Oct 17, 1995Aug 20, 1996The Procter & Gamble CompanyDry cleaning process
US5591236 *Oct 17, 1995Jan 7, 1997The Procter & Gamble CompanyPolyacrylate emulsified water/solvent fabric cleaning compositions and methods of using same
US5630847 *Oct 17, 1995May 20, 1997The Procter & Gamble CompanyPerfumable dry cleaning and spot removal process
US5630848 *Oct 17, 1995May 20, 1997The Procter & Gamble CompanyDry cleaning process with hydroentangled carrier substrate
US5632780 *Oct 17, 1995May 27, 1997The Procter & Gamble CompanyDry cleaning and spot removal proces
US5687591 *Oct 17, 1995Nov 18, 1997The Procter & Gamble CompanySpherical or polyhedral dry cleaning articles
US5804548 *May 20, 1997Sep 8, 1998The Procter & Gamble CompanyDry cleaning process and kit
US5827809 *Oct 15, 1996Oct 27, 1998Vulcan Materials CompanyLow-residue macroemulsion cleaner with perchloroethylene
US5912408 *Jan 24, 1997Jun 15, 1999The Procter & Gamble CompanyDry cleaning with enzymes
US20040261196 *Jun 25, 2004Dec 30, 2004The Procter & Gamble CompanyFabric care compositions for lipophilic fluid systems incorporating an antimicrobial agent
Classifications
U.S. Classification514/244, 510/461, 510/286, 510/383
International ClassificationC11D3/48, D06M16/00, D06L1/04
Cooperative ClassificationC11D3/48, D06L1/04, D06M16/00, Y10S514/942, Y10S514/941
European ClassificationC11D3/48, D06L1/04, D06M16/00
Legal Events
DateCodeEventDescription
Aug 17, 1981AS09Assignment of a part of assignors interest
Owner name: SCHWARTZ, GEORGE C.
Effective date: 19810810
Owner name: WILLIAMS, RITA JANE SCHWARTZ, ROUTE 3, BOX 305 ORL
Aug 17, 1981ASAssignment
Owner name: WILLIAMS, RITA JANE SCHWARTZ, ROUTE 3, BOX 305 ORL
Free format text: ASSIGNMENT OF A PART OF ASSIGNORS INTEREST;ASSIGNOR:SCHWARTZ, GEORGE C.;REEL/FRAME:003887/0073
Effective date: 19810810
Owner name: WILLIAMS, RITA JANE SCHWARTZ, FLORIDA