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Home , Potassium hypochlorite

USOO9233262B2

(12) United States Patent (10) Patent No.: US 9.233,262 B2 Pond et al. (45) Date of Patent: Jan. 12, 2016

(54) DENTAL IRRIGANT 5,719,113 A * 2/1998 Fendler et al...... 510,382 5,739,168 A * 4/1998 Hioki et al...... 514,643 6, 190,542 B1* 2/2001 Comolli et al...... 208/423 (75) Inventors: ARAG, Sw (US) 6,190,642 B1* 2/2001 Dougherty et al...... 424/49 s s 6.255.267 B1* 7/2001 Nayar et al...... 510,191 6,323,171 B1 * 1 1/2001 Fonsny et al...... 510,384 (73) Assignee: Inter-Med, Inc., Racine, WI (US) 7,063,793 B2 6/2006 Albiston et al. 7,070,737 B2 * 7/2006 Bains et al...... 422/37 (*) Notice: Subject to any disclaimer, the term of this 3886. A. : 239: IIKennyth etstal al...... 39. past ised fos lusted under 35 2004f0071748 A1* 4/2004 Asmus et al...... 424/401 .S.C. 154(b) by yS. 2006/0241011 A1* 10, 2006 Renfrow ...... 510,499 (21) Appl. No.: 12/217,601 FOREIGN PATENT DOCUMENTS (22) Filed: Jul. 7, 2008 WO WOO3,061506 T 2003 (Under 37 CFR 1.47) OTHER PUBLICATIONS (65) Prior Publication Data Surface tension conversion, 2011. US 2009/OO88476A1 Apr. 2, 2009 Cameron, Australian Dental Journal, 31, 1996. Jeansonne, Journal of Endodontics, 20, 1996. Related U.S. Application Data Abou-Rass, Oral Surg., 53, 1982.* Shen et al., “Antimicrobial Efficacy of Against Bac (63) y of PE No. 11/998,972, filed on teria in Biofilms at Different Stages of Development'; JOE vol. 37. CC. s s OW aaCOC. No. 5, May 2011; pp. 657-661. (60) Provisional application No. 60/872,107, filed on Dec. Shen et al., “Eval of the Effect of Two Chlorhexidine Prep on Biofilm 1, 2006. Bacteria in vitro: A Three-dimensional Quantitative Analysis'; JOE vol. 35, No. 7, Jul. 2009: pp. 981-985. (51) Int. Cl. Williamson et al., “Antimicrobial Susceptibility of Monoculture AOIN 47/44 (2006.01) Biofilms of a Clinical Isolate of Enterococcus Faecalis', JOEvol. 35, No. 1, Jan. 2009: pp. 95-97. 19.5%" R Shen et al., “The Synergistic Antimicrobial Effect by Mechanical ( .01) Agitation and Two Chlorhexidine Preparations on Biofilm Bacteria'. A61O II/00 (2006.01) JOE vol. 36, No. 1, Jan. 2010; pp. 101-104. A6 IK 8/02 (2006.01) Stojicic et al., “Tissue Dissolution by Hypochlorite: Effect of A6 IK 8/20 (2006.01) Concentration, Temperature, Agitation, & Surfactant”, JOE vol. 36. A6 IK 8/43 (2006.01) No. 9, Sep. 2010; pp. 1558-1562. A6 IK 8/70 (2006.01) A61O 1700 (2006.01) * cited by examiner (52) U.S. Cl. CPC ...... A61o 11/00 (2013.01); A61K 8/0208 Primary Examiner-Susan Tran (2013.01); A61K 8/20 (2013.01); A61K 8/43 Assistant Examiner — William Craigo (2013.01); A61K 8/70 (2013.01); A61Q 17/005 (74) Attorney, Agent, or Firm — Quarles & Brady LLP (2013.01) (58) Field of Classification Search (57) ABSTRACT CPC ...... A61K 6/0032: A61K 6/0035; A61K 6/00 An irrigant comprising either a hypochlorite compound or a See application file for complete search history. chlorhexidine compound in combination with at least one Surfactant and preferably two or more surfactants, including (56) References Cited fluoroSurfactants, ethoxylates, Sulfonates, quaternary ammo nium compounds, amine oxides, and combinations thereof, U.S. PATENT DOCUMENTS wherein each of the Surfactants are capable of complexing 4.919,837 A * 4/1990 Gluck ...... 510,386 with one another. H1467 H 8, 1995 Prieto et al...... 510,340 5,624,891. A * 4, 1997 Smialowicz et al...... 510,195 3 Claims, 7 Drawing Sheets U.S. Patent Jan. 12, 2016 Sheet 1 of 7 US 9.233,262 B2

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US 9,233,262 B2 1. 2 DENTALIRRGANT tion, as this may etch and damage a surface, or cause pain and injury if used during medical or dental procedures. Thus, it is RELATED APPLICATIONS necessary to provide Solutions that are strong enough to treat biofilms without causing irreversible damage. This a continuation patent application of U.S. patent appli There have been several ways discussed to treat biofilms, cation Ser. No. 11/998,972, filed 3 Dec. 2007 now abandoned Such as processes using halogen and oxygen based com , which claims the benefit of U.S. Provisional Patent Appli pounds, including hypochlorite, chlorite, chlorate, and per cation Ser. No. 60/872,107, filed 1 Dec. 2006. oxygen compounds, to treat biofilms. However, especially when treating biofilms related to people and internal Surfaces, BACKGROUND OF THE INVENTION 10 Such as on the dentin of teeth during procedures like root canals, care must be taken so that the treatment process is not The present invention relates to irrigants and dangerous to an individual. Furthermore, treatment of a for Surfaces and, more specifically, irrigants and disinfectants mature biofilm is often unsuccessful because the biocides used for dental and medical procedures and situations. only react with the outer layers of the biofilm and tend not to Dentists, dental Surgeons and dental hygienists and their 15 Sufficiently treat the entire Surface areas, external and inter patients are well aware of the importance of meticulously nal, leaving a healthy and Substantial bacterial community on sterilizing and disinfecting dental instruments. Indeed, since the surface of the substrate, which rapidly regrows. Bacteria dental instruments are used directly in a patient's mouth, within biofilms also develop increasing resistance to biocides Sometimes for invasive or Surgical procedures, it is of para on repeated dosing. It has been found that biocides further mount importance to minimize the presence of microorgan induce cross-resistance to other biocides. isms carried by dental instruments. The microorganisms can A range of bactericidal Substances, commonly termed bio range from relatively harmless bacteria to dangerous patho cides, germicides, or microbicides, are available, all of which gens. Consequently, efforts are deployed to remove microor are claimed by their producers to quantitatively to kill bacte ganisms from dental instruments and from the fresh water ria occurring in aqueous systems. Biocides target a range of lines feeding dental instruments such as air/water Syringes, 25 cellular loci, from the cytoplasmic membrane to respiratory high speed turbines, and ultrasonic scalers, or from saliva functions, enzymes and the genetic material. However, dif evacuation lines. ferent bacteria react differently to bactericides, either due to is universally used as an inherent differences Such as unique cell envelope composi for root canal irrigation, its principal functions in root canal tion and non-Susceptible proteins, or to the development of treatment being microbicidal, dissolving organic material, 30 resistance, either by adaptation or by genetic exchange. Bac and lubrication. However, a disadvantage of sodium tericides should therefore be evaluated against the organisms hypochlorite is that it is highly toxic to human tissues and which they are chosen to control, i.e. the dominant ones in the cells in concentrated form and corrosive and potentially dan system to be treated. The composition of microbial popula gerous to humans at the concentrations at which it is at its tions in Systems varies with the environment, and changes most effective as an irrigating medium. Consequently, Solu 35 considerably after treatment with various biocides by selec tions having low concentrations of sodium hypochlorite are tion for resistant strains. Bacteria growing as biofilms are also generally used, which results in using larger quantities of significantly more resistant to most of the currently known solution than what would be considered ideal quantities of the antimicrobial agents, as compared to planktonic bacteria, Solution. posing ongoing challenges for methods for their control. Similarly, solutions tend to lose their useful properties over 40 In treatment for medical and dental situations, a few solu time. The additives and agents that compose these solutions tions have been developed that are currently used. Examples tend to oxidize rather quickly once they are Subjected to of compounds commonly used in medical treatments include normal environments and Surroundings, which causes the quaternary ammonium compounds, parachlorometaxylenol strengths of Solutions to deteriorate over time and to lose compounds, gluteraldehyde compounds, phenolic com activity. While this deterioration is not necessarily detrimen 45 pounds, such as chlorophenols, , and thymol, peroxy tal for everyday household cleaning and disinfecting, it is acetic aced, , dioxide, chloroxyenols, tetra more pertinent when working with and around skin and tis cyclines, , cresols, caprylic acid, formaldehyde, and Sue. Nonetheless, more stable compounds and Solutions are trichlorosan compounds. While useful, there are still draw still useful in all situations. backs. These compounds can have adverse side effects and Biofilms 50 possible negative impacts if used too often or in too great of Adhesion to surfaces is a common and well-known behav concentrations. Other examples include highly corrosive ior of micro-organisms in many habitats, specifically habitats materials. Such as Sodium hypochlorite, calcium hypochlo where water or other fluids may be present. This adhesion and rite, or other hypochlorite or hypohalogen compounds. Con the subsequent microbial growth lead to the formation of sequently, only small amounts of these materials can be safely biofilms. Bacterial biofilms promote increased biomass depo 55 used on and around humans. However, these compounds also sition, resulting in Surfaces and environments that are less tend to oxidize rather quickly, which reduces the efficacy of than desirous regarding sterility and cleanliness. these compounds over time. Once these compounds are Treatment of biofilms arises in many different environ opened and come into contact with the air, the shelf life for ments and on many differing environments, including treat these products is relatively short due to decomposition of the ment of water Supplies, treatment of medical and dental 60 compounds. To correct for this shortcoming, the strength of equipment, treatment during medical and dental procedures, these compounds ideally would be high. However, as stated and general cleaning and disinfecting of a wide range of above, it is not possible to make the products too strong, or Surfaces. Even though there is a wide range of areas for which they could do severe damage to a patient. treatment may be necessary or desirous, there are also some The prior art does not adequately provide a stable agent that common factors to take into account. Treatment compounds 65 maintains acceptable stability after storage times and storage and solutions must not be too corrosive for their intended conditions typical of actual usage conditions encountered in uses. For example, you would not use an overly strong solu the real world. For instance, most commercial product distri US 9,233,262 B2 3 4 bution channels result in products aging several months fol cesses, which may include intricate steps, are carried out so lowing manufacture before being placed on sale, followed by that the compound has a suitable and useful equilibrium. significant delays before actually being used. During this However, in forming a stable solution or compound some of time, products are seldom Stored under ideal conditions, but the efficacy of the system may be lost. rather are exposed to temperature variations typical of the Thus, it would be advantageous to develop compounds and home, field and industrial environment. systems for medical, dental, and general cleaning solutions Many typical commercially sold bleach products contain that have increased stability without overly affecting the effi ing hypochlorite solutions have a half-life of around six cacy of the Solution. months or less. This stability is generally sufficient for every day household cleaning chores and duties. In medical and 10 SUMMARY OF THE INVENTION dental situations better stability is desired, especially when other compounds are added to the hypochlorite Solutions. The present invention is directed towards irrigation and When wetting agents, Surfactants, penetrating agents, and/or disinfection solutions. The Solutions comprise disinfectants other similar additives and active agents are added to the combined with Surfactants or Surface agents, wherein the hypochlorite solutions, stability and efficacy is lost due to 15 Surfactants are capable of complexing with one another. The oxidation of the agents. result is Solutions having synergistic effects. Other treatment solutions and detergent compositions in The solutions have enhanced properties that were previ the medical and dental field are known in the art. Chlorhexi ously not attainable in the art, such as enhanced leveling, dine based compounds are one class of compounds used in wettability, Suspension, and emulsification, among other biocide Solutions and antimicrobial Solutions. properties. Furthermore, the solutions have improved stabil Chlorhexidine is used to prevent and treat the redness, ity compared to the industry standard Solutions, which was an Swelling, and bleeding of the gums associated with gingivitis. unexpected result. Since the solutions are more stable, the It is classified as a antimicrobial drug. Chlorhexi efficacy of the solutions are more consistent over extended dine is generally accepted to be effective as an antiseptic hand periods of time compared to the standard Solutions previously wash for methicillin-resistant Staphylococcus aureus 25 used in the art, which leads to a better shelf life than those (MRSA). Chlorhexidine is obviously an easily tolerated and Solutions. This can lead to an economically advantageous effective antiseptic for the daily practice of medicine and Solution, as potentially less Solution is needed for a procedure Surgery. Its oral use is also well documented (e.g. in ill Sub compared to previous Solutions. jects who cannot brush their teeth adequately). However, the Generally, the Solutions are comprised of a disinfectant in teeth discolorations that are caused by the drug are disturbing. 30 combination with a basic or polar solvent compound. The Chlorhexidine is an antiseptic agent effective against Solutions further comprise at least one Surfactant, and prefer plaque, oral flora including Candida sp. and Candida albi ably two or more surfactants. cans, and is used as a cleanser for Surgical Scrub, skin wounds, The present invention also comprises a dental irrigant that germicidal hand rinse, and as an antibacterial dental rinse. has improved efficacy features and qualities compared to the Chlorhexidine is active againstgram-positive and gram-nega 35 prior art, while also being a sufficiently stable product. The tive organisms, facultative anaerobes, aerobes, and yeast. irrigant comprises an aqueous Solution containing a disinfec Chlorhexidine is essentially nontoxic when applied to the tant, such as Sodium, calcium, , or lithium skin or mucous membranes, compared with disinfectants hypochlorite (NaOCl, CaOCl, KOCl, LiOCl) and similar including cresol, bleaching powder, and which are, in hypochlorite compounds in combination with a strong base, general, toxic to cells of the body. Other common antiseptic 40 Such as a hydroxide compound. The composition further agents include , , hexachlo includes Surfactants that contain ethoxylates, more specifi rophene, iodine compounds, compounds (i.e. thime cally alkylphenolethoxylates and alcoholethoxylates. The rosal), alcohol and , hexamine hippurate, compositions have improved performance qualities over the , , and . Other prior art. For instance, compared to currently used wetting Substances which can be used for antiseptic purpose include 45 agents, the Solution of the current compositions have boric acid and Volatile oils such as methyl salicylate and some improved wetting and leveling qualities, and also improved botanical essential oils. penetration and digestibility, and breaks down biofilms more and benzalkonium chloride are used pri efficiently. The solution also has a longer shelf life compared marily in hand or face washes. Benzalkonium chloride must to the prior art, which results in the Solution having a more not be applied to areas which have not been fully rinsed as it 50 consistent potency after the solution comes into contact with is inactivated by organic compounds. Benzalkonium applica air. The composition comprises approximately up to 8% of tion may include disinfecting instruments and preserving the hypochlorite compound, up to about 2% of the basic drugs in low concentration form. Aqueous iodine solutions compound, and up to about 2% of the ethoxylate compound. are less effective than alcoholic solutions, but the drying Other Surfactants may be present in the irrigant. effect of the alcoholic component can be irritating to abraided 55 The present invention further provides an improved skin. Povidone iodine is convenient to use as it is less irritat method of irrigating dental Surfaces, such as root canals and ing, but not as effective. the like. With the use of the improved surface treatment agent Chlorhexidine is also used as a safe antiseptic or disinfec or Surfactants, wetting agent, penetrating agents, or leveling tant application to prevent body infection and in oral rinses agents of the present invention, it is possible to more effi for treating Sore gums, mouth ulcers, periodontal and endo 60 ciently treat and clean dental cavities, such as root pulp canals dontic infections, and preventing plaque on teeth. It is used in and caries. These surface agents also are referred to as Surface the form of acetate, gluconate or hydrochloride, either alone modifiers. or in combination with other compounds, such as cetrimide. The present invention also contemplates the use of stable However, these chlorhexidine compounds have a tendency to chlorhexidine solutions that can be used for a wide variety of gel or coagulate when agents, such as Surfactants, wetting 65 situations, including medical and dental uses, general clean agents, leveling agents, penetrating agents and the like, are ing and antiseptic uses, treating and disinfecting of water added to the compounds. To prevent clotting or gelling, pro lines, and used in commercial products. Such as sprays and US 9,233,262 B2 5 6 wipes. The Solutions and products generally comprise at least The main active ingredient of the solution as shown in Table a tertiary compound, which will be discussed in further detail. 1 is a hypohalogen compound. Possible solutions include The solutions can also be used as an improved disinfectant, Sodium, lithium, calcium, or potassium hypochlorite solu in general, and for specific purposes, such as disinfecting and tions, or generally alkali or alkaline earth metal hypohalogen cleaning water lines. These and other improvements will 5 compounds, such as hypobrimide, as is known and under become more evident with the detailed description below. stood by the art. One source for the chlorite compound comes from bleach, such as CloroxR) bleach, manufactured by The BRIEF DESCRIPTION OF THE DRAWINGS Clorox Company. As an example, a Sodium hypochlorite test Solution containing 6% sodium hypochlorite was found FIGS. 1-9 demonstrate a first method for mixing a solution 10 adequate to perform in accordance with the present invention. in accordance with the present invention. The hypochlorite compound preferably has a pH in the range FIGS. 10-18 demonstrate a second method for mixing a Solution in accordance with the present invention. of 10.50-13.50. FIGS. 19-22 demonstrate a method of producing a disin A strong basic compound, such as sodium hydroxide fectant wipe that incorporates a solution produced in accor 15 (NaOH) or (KOH), is also present in the dance with the present invention. solution. In the example depicted in Table 1, sodium hydrox ide (NaOH) is present in the compound or solution, with DESCRIPTION OF THE PREFERRED between 0.01% and 2% of the weight of the solution, with the EMBODIMENT NaOH either being introduced as an aqueous solution or in powder form. Although the disclosure hereof is detailed and exact to In a preferred embodiment of the solution, the solution enable those skilled in the art to practice the invention, the further comprises an ethoxylate compound, such as octylphe physical embodiments herein disclosed merely exemplify the nol ethoxylate or nonophenol ethoxylate. Approximately invention which may be embodied in other specific structures. 0.01%-20% of the phenol ethoxylate will be used in the While the preferred embodiment has been described, the 25 present invention. Preferred ethoxylate compounds include details may be changed without departing from the invention, alkyl phenol ethoxylates, phenol ethoxylates, alcohol ethoxy which is defined by the claims. lates, also called synthetic or fatty alcohol, and related or Disinfectant and irrigant solutions according to a first similar compounds and combinations thereof. Below is a embodiment of the present invention generally comprise general formula for octylphenol ethoxylate: three separate compounds or compound groups: (1) a disin fectant, preferably a hypohalogen , Such as a hypochlorite 30 compound; (2) a strong alkali or basic compound, such as sodium hydroxide (NaOH) or potassium hydroxide (KOH): and (3) a Surfactant compound or compounds. A strong basic compound is a Substance which completely hyrdolyzes and disassociates in an aqueous system and raises the pH of water 35 from about 7.0 to 14.0. The surfactants, also called surface agents, generally are selected from ethoxylates, fluoroSurfac tants, Sulfonate Surfactants, polyglucosides, amine oxides, R in the above formula preferably is a carbon chain between and other similar compounds known and used in the art. The Cs and C. Similar commercial solutions, such as TritonTM Surfactants are provided in the solution in a manner that they 40 X-100 Surfactant and TRITONTM CG-110 Surfactant, both will complex with one another, thereby providing synergistic produced and sold by the Dow Chemical Company (“Dow'), effects for the solution overall. are manufactured, with the “X” generally indicating the num Table 1 provides a breakdown of one possible first embodi ber of moles of the ethoxylate or alcohol ethoxylate in the ment of a composition for the treatment solution of the product or solution. TritonTMX-100 contains approximately present invention. The Solution is an aqueous based solution. 45 100 moles of alcohol ethoxylate. TRITONTM CG-110 con The percentages given are weight percentages. However, it is tains approximately 110 moles of an alkyl polyglucoside understood that other percentages and ranges may be used compound. In the Solution according to the present invention, and fall within the scope of the present invention. Likewise, there are approximately 3-15 moles of the noted ethoxylate other surfactants may be incorporated into the solution, or compounds present, with a more preferred amount being may replace one of the listed Surfactants. As an example, it is 50 around 9-11 moles. possible to replaced the phenolethoxylate surfactant listed in Table 1 with a different surfactant, such as an ammonyx-LO Another possible ethoxylate surfactant is TERGITOLTM (N,N-dimethyldodecylamine-N-oxide) surfactant, and the 15-S-7, also purchased from Dow, which is a secondary alco solution would still fall within the scope of the present inven hol ethoxylate nonionic surfactant. TERGITOLTM 15-S-7 is tion. soluble in water, soluble in chlorinated solvents and most 55 polar organic solvents. It is also stable in the presence of dilute acids, bases, and salts, and is compatible with anionic, TABLE 1. cationic, and other nonionic Surfactants. Weight Percentage of The solution further comprises another surfactant, prefer Component Overall Composition ably a Sulfonate Surfactant, comprising approximately Water 99.5%-83.0% 60 0.01%-5.0% of the weight of the solution. The preferred Sodium Hypochlorite (NaOCl) O.O1%-10.0% Surfactant is soluble in water and highly soluble in strong acid Sodium hydroxide (NaOH) O.O1%-2.0% and alkali solutions. A mixture of decylbenzene Sulfonic acid Commercial grade O.O1%-2.0% or benzene sulfonic acid with a disodium salt would be such phenolethoxylate Surfactant Sulfonate surfactant O.01%-5.0% a Surfactant. Generally, diphenol Sulfonates, alkyl aryl Sul fluorosurfactant O.O1%-2.0% 65 fonates, aryl Sulfonates, alkyl Sulfonates, both branched and unbranched, and diaryl Sulfonates, and combinations thereof are acceptable as Surfactant. One example of such a surfactant US 9,233,262 B2 7 8 is alkyldiphenyloxide disulfonate, sold as Dowfax C1OL by and is a viscous, water-soluble yellow liquid. The hydrophilic Dow. However, other compounds may also be included, such groups in this compound are polyethers also known as poly as amine oxides having a general formula of oxyethylene groups which are polymers of ethylene oxide. In the nomenclature of polysorbates, the numeral designation following polysorbate refers to the lipophilic group, in this case the oleic acid. However, as noted earlier, the Surfactant tends to gel when introduced into a chlorhexidine compound. Thus, prior art did not allow a combination of the compounds in effective, useful amounts. Similarly, other Surfactants, such 10 as fluorotelomers, were not easily and usefully introduced Where R. R. and Rs are preferably carbon chains between into such a solution, as they also immediately reacted with the Cs and Cs, and more preferably carbon chains between Co chlorhexidine. and C14. The present invention addresses this problem by introduc The preferred embodiment of the solution also includes a ing a tertiary Surfactant system. The Surfactants include Sugar fluorosurfactant, comprising approximately 0.01%-2% of the 15 ester Surfactants, glucoside Surfactant, including alkyl gluco solution. Preferred surfactants are fluorotelomer of fluoroli sides and similar glucosides, and fluorinated Surfactants, gomer monoethers, usually arranged with a polyethylene gly similar to the Surfactants discussed in the prior embodiment col (PEG) compound. These ethoxylated nonionic fluorosur of the invention. The present solutions provide blended solu tions made by combining individual solutions, which consist factants give exceptional low aqueous Surface tensions at of diluted amounts of the various surfactants. concentrations as low as 0.002% (20 ppm). This type of Thus, a first solution is prepared with the Sugar ester. As an fluorotelomer has a general structure of example, an aqueous solution containing approximately 12% Tween 80 by weight was prepared. A second aqueous solution Where was prepared containing approximately 20% by weight of an Rf-F (CFCF)y 25 alkyl glucoside compound. Finally, a third aqueous solution X=0 to about 15 containing approximately 2% by weight of a fluorotelomer Y=1 to about 7 was prepared. An example of a fluorosurfactant is DuPontTM Zonyl(R) FSO, These solutions were combined together in another final a fluoroalkyl alcohol substituted monoether combined with aqueous Solution, preferably in equal amounts, preferably , which is produced and manufactured by 30 with each Solution comprising approximately 1% by weight the DuPont Company. The compound is an ethoxylated non of the total solution. The final solution contained a chloro ionic fluorosurfactant that is generally considered to have hexidine compound, such as chlorhexidine gluconate com effective emulsifying and dispersing qualities and highly pound, which comprised approximately 10% of the solution. effective wetting qualities. The final solution maintained bioefficacy and stability for the The overall solution has a pH within the range of 10.5 to 35 Solution, had stable wetting, leveling, and penetrating quali 13.5. It should be noted that the above values are exemplary ties, and also maintained Sufficient conductivity. Further and that each of the specific compounds can fall within a more, the solution did not clot or gel as would have been certain range. For instance, NaOCl could be within the range expected from the prior art. of 0.02% to 8.0%. Additionally, alternate chlorite compounds The amounts given are just examples and should not be may be used, including alkali earth metal and/or alkaline 40 considered as limiting the ranges at which the Solution prop earth metal hypohalogens selected from the group consisting erly performs. Provided that a chlorhexidine compound can of sodium hypochlorite, potassium hypochlorite, magnesium be combined with various surfactants to provide a usable hypochlorite, , , solution that will not unduly clot or gel and will retain suffi and mixtures thereof. cient beneficial properties, the compound would fall within Similarly, other strong basic compounds could be used 45 the scope of the present invention. instead of NaOH, including other alkalines, i.e. KOH, For example, it has been determined according to the MgOH, LiOH, CaOH and mixtures thereof. The amount of present invention that chlorhexidine compounds can be com the hydroxide can range from 0.02 to 2.00%. bined with other chelating agents or compounds to form As stated above, different ethoxylates, preferably alkyl stable solutions. One example is a combination of a chlo phenol ethoxylates, are present in the current invention, hav 50 rhexidine gluconate compound (CHG) with ethylenedi ing an approximate range of between 3 and 18 moles of aminetetracetic acid, commonly referred to as EDTA. Gen ethylene oxide. erally, mixing CHG with EDTA formed a white precipitate or The present invention can incorporate a wide range of flocuculant. Other combinations include CHG with citric Surfactants, including anionic, cationic, and nonionic Surfac acid. Preferred embodiments of these solutions are shown tants, and potentially amphoteric, and Zwitterionic Surfac 55 below in Table 1A. The individual compounds are listed as a tants. As noted above, Surfactants and Surface agents of par percentage of the overall solutions. ticular interest are fluorinated telomers and derivatives thereof. TABLE 1A The present invention also provides another improved wet ting, leveling, and/or penetrating compound or Solution. In 60 Chlorhexidine Solutions this embodiment, the solution comprises a chlorhexidine CHG with citric compound, preferably a chlrohexidine gluconate compound, Compound CHG with EDTA acid with a Sugar ester Surfactant. One Such surfactant is Tween(R) CHG 3.00% 10.00% 80. Tween R 80 (Polysorbate 80) is a hydrophilic nonionic EDTA 1.00% NA Surfactant commonly used as an ingredient in dosing vehicles 65 Citric Acid NA 2.00% for pre-clinical in vivo studies (e.g., pharmacokinetic studies, Triton CG-110 3.04% 2.00% etc.) It is derived from polyoxylated sorbitol and oleic acid, US 9,233,262 B2 9 10 TABLE 1A-continued with 435.8+0.1 g of a second surfactant 18, preferably Triton CG-110, and then set aside. As noted with the first surfactant Chlorhexidine Solutions 14, a pipette or syringe may be used for measuring an accurate CHG with citric amount of the surfactant 18. Compound CHG with EDTA acid FIG.3 shows a third beaker 20 placed on the scale 12, and the scale 12 is tared to zero. The third beaker 20 is filled with Zonyl FSO (aqueous 2.0% NA solution) 858.7+0.1 g of a third surfactant 22. As an example, an aque HO 90.16% 83.00% ous Solution containing 2.5% of a fluoroSurfactant could com Tergiitiol 15-S-7 NA 2.00% prise the third surfactant 22. Similar to the measurement of Ammonium hydroxide 2.20% NA 10 the previous Surfactants, a pipette or syringe may be used for measuring an accurate amount of the Surfactant 22. As with the other discussed solutions, the listed values are In FIG.4, distilled water 24 is added to a large mixing tank merely exemplary and other ranges of compounds and Sur 26. The tank 26 is preferably a Nalgene cylindrical tank, but factants will fall within the scope of the present invention. any tank having a sufficient Volume may be used. Twenty (20) 15 gallons of water 24 is added to the tank. A mixer 28 is inserted Provided that a chelating compound or solution allows for the into the tank to 26 provide agitation. The mixer 28, which can added Surfactants to complex with one another, and with the be any mixer known and used in the industry, such as the chelating agent or the chlorhexidine compound, the resultant mixers produced by The Barnant Company, is started, thereby solution will fall within the scope of the present invention. agitating the water 24. The present solutions are also believed to have potentially FIG. 5 demonstrates that the first surfactant 14 is slowly improved qualities when an electrical current is introduced added to the distilled water 24 in the tank 26, and the solution together with the solution. When the charge is applied, nega is further agitated for approximately one (1) minute. tive of an antimicrobial agent may be encouraged to In FIG. 6, the second surfactant 18 is slowly added to the diffuse toward an applied positive pole, which may help the mixture of FIG. 5, and is further agitated one (1) minute. present solutions to penetrate into Small tubules and crevices. 25 In FIG. 7, the third surfactant 22 is slowly added to the Electrical stimulation is also known to make biofilms more mixture of FIG. 6 and allowed to agitate. susceptible to chemical disruption. Furthermore, with the While the mixture agitates, a container 30, possibly a plas high conductivity of hypochlorite based solutions combined tic pitcher, is placed on the scale 12 and tared to Zero, as is with an electrical current allows for more rapid debridement demonstrated by FIG. 8. The container 20 is filled with an of organic material compared to the prior art. It is also 30 aqueous chlorhexidine Solution 32. One Such solution is an believed that the present invention and solutions will have aqueous solution containing chlorhexidine gluconate (20% improved qualities when treated with other mediums, such as w/v). 8580+0.1 g of the chlorhexidine solution 32 is weighed heat and light. As an example, it may be possible to introduce out and added to the tank 26. The mixture is further agitated the Solutions, specifically the chlorhexidine gluconate solu for one (1) minute. tion, to an iontophoretic process to further increase the effi 35 Finally, as demonstrated in FIG.9, a dye 34 can be added to cacy of the solution. the tank 24, if desired. A small amount of dye 34 is sufficient The solution has other improvements over the prior art. The to provide coloring for the mixture. In the present example, an Solution also can be used for a wide range of uses, such as aqueous dye Solution comprising methylene blue chloride general cleaning and disinfecting, sterilizing of medical and (1% w/v), approximately 40 g of the dye solution, is added to dental equipment, and cleaning of fluid lines. The Solutions 40 the mixture. Agitation continues, approximately twenty min can also be incorporated into cleaning Supplies. Such as dis utes, until the dye 34thoroughly dissipates through the mix infectant wipes. The improved stability and consistent ture, though other mixing times may be used. The final solu strength of the solution will provide cost savings compared to tion 50 was tested and the results are listed, as follows. prior art solutions. That is, because the solutions will retain a Results longer stability than prior art and be efficacious over a longer 45 Various solutions were prepared similarly to the above time compared to the prior art, less amount of the Solution will procedure, which includes a chlorhexidine compound be used. Thus, even if the cost to make the solutions is higher according to the present invention. These solutions were than current Solutions used, the amount of solution used for a tested for various qualities, such as pH, Surface tension, con specific task will be smaller than the prior art amount, which ductivity, specific gravity, and the color of the Solutions. will lead to lower costs overall. 50 Generally, the tests were carried out between about 75° and Sample Solutions 78°F. These solutions were tested against the current industry Batch solutions were produced in accordance with the standards and are listed below in Table 2. above criteria and were compared to current products and standards of the industry. Solutions can be prepared as fol TABLE 2 lows: 55 Solutions Containing Chlorhexidine Compounds

EXAMPLE1 Test Test Current Characteristic Solution 1 Solution 2 Standard FIGS. 1-9 demonstrate a procedure for mixing a first solu pH 5.64 5.64 S.62 tion according to the present invention. In FIG. 1, the solution 60 Surface 26 dynes/cm 26.3 dynesicm 47 dynesicm is initially prepared by placing a first beaker 10 on a scale 12. Tension The scale 12 is tared to Zero and the first beaker 10 is filled Conductivity 1590 mSmcm 1585 mSmcm 1522 mSmcm Specific 1.038 grams/cm 1.037 grams/cm 1.040 grams/cm with 157.4+0.1 g of a first surfactant 14, preferably Tergitol Gravity 15-S-7, and then set aside. A pipette or syringe may be used if Color (human Same as Same as NA necessary to get an accurate amount of the first Surfactant. 65 observation) standard standard In FIG. 2, a second beaker 16 is placed on the scale 12, and the scale 12 is tared to zero. The second beaker 16 is filled US 9,233,262 B2 11 12 The results showed that the solution generally met or surfactant may comprise the third surfactant 126. Similar exceeded current industry standards. The Surface tension was with the previous Surfactants, a pipette or Syringe may be used significantly decreased, which leads to improved leveling and for measuring an accurate amount of the Surfactant 126. wettability qualities. In FIG. 14, a hypochlorite solution 128 is added to a large Freeze Thaw Cycle Stability Studies: 5 mixing tank 130. The tank 130 is preferably a Nalgene cylin The above Test Solutions were tested to determine the drical tank, but any tank having a Sufficient Volume may be stability of the solutions. Each of the solutions was tested used. Approximately 4/4 gallons of hypochlorite solution 128 three times, with the value averaged for each solution. Open is added to the tank, such as 4/4 gallons of commercially sold weighing dishes were used to freeze the Solutions. The weigh CloroXCR bleach. A mixer 132 is inserted into the tank 130 to ing dishes were made of Pyrex glass, having a diameter of 8 10 provide agitation. The mixer 132, which can be any mixer cm and a depth of 2.5 cm. 50 grams of each solution were known and used in the industry. Such as the mixers produced frozen and then thawed, with the results given below. by The Barnant Company, is started, thereby agitating the Results hypochlorite solution 128. 1) The solutions were within the limits of acceptable stability In FIG. 15, the basic solution 114 is slowly added to the for dental solutions. That is, the test solutions indicate that 15 hypochlorite solution 128 and the solution is further agitated they would meet the required properties for standard irrigants for approximately one (1) minute. currently in use in the related dental and medical fields. In FIG. 16, the first surfactant 118 is slowly added to the Hypochlorite solutions prepared similar to the above proce mixture of FIG. 15 and is further agitated one (1) minute. dure were further tested for stability. In FIG. 17, the second surfactant 122 is slowly added to the 2O mixture of FIG. 16 and allowed to agitate. EXAMPLE 2 Finally, in FIG. 18 the third surfactant 126 is slowly added to the mixture of FIG. 17, and is further agitated for twenty FIGS. 10-18 demonstrate the preparation of a second test minutes so that all the individual compounds are thoroughly Solution prepared according to the present invention. In FIG. mixed, but other mixing times are possible. The final solution 10, a first beaker 110 is place on a scale 112. The scale 112 is 25 150 was tested and the results are listed, as follows. tared to zero and the first beaker 110 is filled with a basic Various solutions prepared according to the second proce Solution 114. Such as an aqueous Sodium hydroxide Solution dure, which includes a hypochlorite compound, were tested (50% w/v), and then set aside. A pipette or syringe may be for various qualities, such as pH, surface tension, conductiv used if necessary to get an accurate amount of the basic ity, specific gravity, and the color of the solutions. Generally, solution 114. Preferably 93.0+0.1 g of the basic solution 114 30 the tests were carried out between about 75° and 78°F. These is measured. results are listed below in Table 3. TABLE 3 Solutions Containing Hypochlorite Compounds

Test Test Test Test Test Quality Solution 1 Solution 2 Solution 3 Solution 4* Solution 5 pH 1238-1246 12.48 12.38 1249-12.51 12.41 Surface 29.82-31.7 dynesicm -29 dynes/cm 30.41 dynes/cm 29.82-31.7 dynesicm 30.2 dynesicm Tension Specific 1.108 g/cm 1.113 g/cm 1.108 g/cm 1.104 g/cm 1.106 g/cm Gravity Conductivity 128.3-132.9 mSmcm -130 mSmcm 131.2 mSmcm 131.2 mSmcm 130.2 mSmcm Available 5.82%-6.01% (v/v) 6.05% (v/v) 5.84% (v/v) 5.82%-5.87% (v/v) 5.95% (v/v) Chlorine Color Clear light Aqua clear to Aqua clear to Clear light Clear light Straw color, light straw light straw straw color, straw color, no visible color, no color, no no visible no visible particles visible visible particles particles particles particles *Test Solution 4 included three separate solutions, with the range of results given.

FIG. 11 shows a second beaker 116 being placed on the The results were consistent with the characteristics of current scale 112, and the scale 112 is tared to zero. The second solutions in the art. Further, the surface tension and available beaker 116 is filled with 92.8+0.1 g a first surfactant 118, chlorine showed improved qualities over the prior art. The preferably Dowfax C1OL, and then set aside. As noted with 55 color of the solutions matched the standards in the art, with the basic solution 114, a pipette or Syringe may be used for the color tested by using an HP model 8453 UV-VIS spectro measuring an accurate amount of the first Surfactant 118. photometer. Solutions prepared similar to the second proce FIG. 12 shows a third beaker 120 being placed on the scale dure were further tested to determine stability of the solu 112, and the scale 112 is tared to zero. The second beaker is tions, using a freeze thaw method, similar to the method used, filled with 97.0+0.1 g of a second surfactant 122, preferably 60 above. Triton X-100, and then set aside. As noted with the previous compounds, a pipette or Syringe may be used for measuring Freeze Thaw Cycle Stability Studies: an accurate amount of the second surfactant 122. Hypochlorite solutions prepared according to the present FIG. 13 shows a fourth beaker 124 being placed on the invention were tested against a standard industry disinfectant, scale 112, and the scale 112 is tared to zero. The fourth beaker 65 a CloroxR bleach product produced by The Clorox Company. 124 is filled with 184.1+0.1 g of a third surfactant 126. As an Both solutions contained sodium hypochlorite. The test was example, an aqueous solution containing 2.5% of a fluoro carried out as follows: US 9,233,262 B2 13 14 Three sixty gram samples of a hypochlorite solution and Comparative Example 4 three sixty gram samples of the Clorox(R) product were poured into separate two (2) ounce glass bottles. The samples were frozen and then thawed. The average results are given below. Results: Distilled Water: 97.99% The solutions prepared according to the present invention Methylene Blue Chloride (1%): OO.01% had no visible particles or Suspended solids once the solutions Chlorhexidine Gluconate: O2.00% were thawed. The CloroxR) product had visible suspended particles upon thawing and, also, had a visible heavy haze. The characteristics of the solutions were compared and This indicates that the solutions according to the present 10 recorded in the following table. The leveling and wettability invention have comparatively better stability. were determined by evenly coating a pre-determined area of After three inversions after thawing, striation disappeared flat glass surface with a pre-determined amount of milliliters in the Solutions according to the present invention. The Clo of each Comparative Example at 25°C. The coated film was roxR) product required six inversions after thawing for the observed for its continuity and maintenance of its leveling striation to disappear. Striation is the visible separation of the 15 characteristic for a period of 60 seconds. different compounds within a solution that is commonly Suspension and emulsification characteristics were deter scene after a solution is frozen. Inversion is flipping the con mined by placing a sample of 20 milliliters of each Compara tainer containing the solution and then uprighting the con tive Example in a 100 mL graduated cylinder. Into each tainer, to provide for the striated compounds to remix with sample, ten drops of household oil were introduced into the one another. The results demonstrate that the solution accord graduated cylinders. The cylinder was inverted twenty-four ing to the present invention show improved Stability accord times vigorously at room temperature, and the samples were ing to known solutions, as they remix quicker than the known observed when the cylinders were in the upright position until Solutions. the separation of Suspension and emulsification occurred. The The pH for the solutions according to the present invention Surface tension of each sample was tested twice. The occur did not change after thawing. The CloroxR product had a pH 25 drop of 0.25 from 12.85 to 12.60 after thawing. This also rence of separation was timed in minutes. shows that the present invention has improved stability com pared to the industry standard. TABLE 1 Comp. Comp. Comp. Comp. COMPARATIVE EXAMPLES 30 Ex. 1 Ex. 2 Ex. 3 Ex. 4 Surface 3O4 26 39 47 The following comparative examples were used to com Tension 29.0 26.3 38 46 pare the properties of Solutions according to the present (Dynes/cm) invention to standard solutions in the industry. Comparative pH 12.75 5.95 12.SO 5.64 Leveling and 100% 100% 85% 80% Examples 1 and 2 are based on the present invention and 35 Wettability Comparative Examples 3 and 4 are standard solutions of the Suspension and 3 minutes 2 minutes 1 minute 1 minute industry. Emulsification 45 seconds 4 seconds 15 seconds Conductivity 128-133 1590 Not 1522 Comparative Example 1 (mS/cm) Tested 40 As indicated in the table, Comparative Examples 1 and 2. Bleach 6% Sodium Hypochlorite (NaOCl): 97.50% formulated according to the present invention have Superior Sodium Hydroxide (50%): O2.00% ity qualities and properties over the Comparative Examples 3 Dowfax C-1OL (anionic detergent): OO.15% and 4, specifically the qualities of Surface tension, leveling Triton X-100 (nonionic detergent): OO.20% 45 and wettability, Suspension and emulsification and conduc Fluorosurfactant (2.5%): OO.15% tivity. As the Surface tension of a solution is lowered (given in dynes percentimeter for Comparative Examples 1 and 2), the ability of the solution to effectively wet the exposed surface is Comparative Example 2 increased. The presence of the different Surface active agents 50 in Comparative Examples 1 and 2 contribute in producing Superior performance of Comparative Examples 1 and 2 over the performance of Comparative Examples 3 and 4 (standard Distilled Water: 95.97% Tergitol 15-S-7 (nonionic): OO.20% Solutions). Triton CG-110 (nonionic): OO.S5% Products Fluorosurfactant (2.5%): O1.10% 55 The potential products that the solutions could be used with Chlorhexidine Gluconate: O2.17% are numerous. For instance, the Solutions can be used during Methylene Blue Chloride (1%): OO.01% medical and dental procedures, used for disinfecting medical and dental equipment, used for cleaning and declogging water lines and pipes. The Solutions could also be incorpo Comparative Example 3 60 rated into general cleaning solutions, individual wipes, towels and towelettes, as sprays and other disinfectants, as hand sprays and hand sanitizers and many other cleaning, disin fecting, and treatment Solutions. Bleach 6% Sodium Hypochlorite (NaOCl): 97.50% Sodium Hydroxide (50%): O2.00% Wet Surface Disinfectant Distilled Water: OO.S.0% 65 Solutions according to the present invention have been developed to act as Surface disinfectants or disinfectant sprays. The disinfectants generally comprise an aqueous US 9,233,262 B2 15 16 Solution comprising surfactants in combination with a chlo Semi-Anhydrous Wipe rhexidine compound. More specifically, the solution com Semi-anhydrous, or dry wipes, are formed similar to the prises a chlorhexidine gluconate compound in combination wet wipes, except that the wipes would be impregnated with with surfactants, with the formula being like that shown in the semi-anhydrous surface disinfectant as opposed to the wet 5 surface disinfectant. Semi-anhydrous wipes would beformed Comparative Example 2, above. It has been determined that similar to that described for the wet wipes. the chlorhexidine gluconate compound in the disinfectant The present invention embodies improved solutions that could make up to about 20% of the solution and provide a can be employed for a wide variety of uses. Further, the stable solution that will have desirous disinfectant effects. Solutions can be incorporated into a wide range of products. Disinfectant Wipes Provided that a solution formulated according to the present Disinfectant wipes can be formed using the solutions 10 invention is used for cleaning and disinfecting purposes, it is according to the present invention. FIGS. 19-22 demonstrate understood that the solution and the medium used would fall a method for forming a disinfectant wipe incorporating solu within the scope of the present invention. tions according to the present invention. Preferably, wipes are The present invention provides classes of disinfectants and impregnated with the chlorhexidine gluconate solutions irrigants that combine surfactants in a manner so that the according to the present invention. 15 surfactants will complex with one another and, also, with the In FIG. 19, a flat container 200 is filled with a solution 202 main disinfectant of the solution. Provided that the discussed formed according to the present invention. One example of a Solutions, surfactants, and other compounds complex with container is a basingenerally used when painting with a paint one another, it is understood that such combinations in a wide roller. A non-woven fabric 204 is place within the container range of percentages will fall within the scope of the present 200, as shown in FIG. 20, and the fabric 204 soaks up the invention. solution 202. The fabric 204 is removed from the container, The foregoing is considered as illustrative only of the prin and any excess solution 202 is removed from the fabric 204. ciples of the invention. Furthermore, since numerous modi For example in FIG. 21, a paint roller 206 is used to remove fications and changes will readily occur to those skilled in the the excess solution. That is, the paint roller 206 is moved back art, it is not desired to limit the invention to the exact con and forth over the fabric 204, thereby providing a squeegee 25 struction and operation shown and described. While the pre ferred embodiment has been described, the details may be effect to remove excess solution from the fabric 204 changed without departing from the invention, which is In FIG. 22, the fabric is then placed in a container 208 that defined by the claims. will prevent the fabric 204 from drying out. It is understood We claim: that any commercially available container known and used in 30 the industry will suffice as the container 208. It is further 1. An irrigant and disinfectant solution for medical and understood that the described process is merely exemplary of dental uses obtained in a process comprising the steps of: a process for making a disinfectant wipe. It is further under adding a first solution comprising a strong basic compound stood that other processes known and used in the industry, Selected from the group consisting of potassium hydrox especially processes for mass producing wipes, can be ide, sodium hydroxide, lithium hydroxide, and combi 35 nations thereof, to a second solution comprising a hypo employed to produce wipes according to the present inven halogen salt and agitating to provide a first mixture; t1On. adding an alkyldiphenyloxide disulfonate surfactant to the Semi-Anhydrous Surface Disinfectant first mixture and agitating to provide a second mixture: Drying style disinfectant sprays have also been formulated adding an alkylphenol ethoxylate surfactant to the second according to the present invention. The formulas are gener 40 ally the same as the wet surface disinfectants, with a portion mixture and agitating to provide a third mixture; and of the water, a polar solvent, in the solution being replaced adding a fluorosurfactant to the third mixture and agitating with an alcohol compound. For example, the formula shown to provide an irrigant and disinfectant solution compris above in Comparative Example 2 would be similar for a dry 1ng: disinfectant, except a portion of the distilled water would be about 0.1-10.0 weight percent of the hypohalogen salt: replaced with an alcohol compound. In one preferred embodi 45 about 0.01% - 3.00 weight percent of the strong basic ment, approximately ~70% of the distilled water would be compound; and replaced with an alcohol compound, preferably, denatured about 0.1-2.0 weight percent of the alkylphenolethoxy 40-B, with approximately ~25% distilled water late surfactant. remaining in the formula. In a preferred embodiment, the 2. The irrigant and disinfectant solution according to claim solution will comprise approximately 5% water with an alco 50 1 wherein said pH of said irrigant and disinfectant solution is hol content between 68% and 95% of the solution. In a more about 10.50 - 13.50. preferred embodiment, the alcohol content will be between 3. A disinfectant wipe comprising the irrigant and disin 70% and 85% of the solution. As is known in the art, various fectant solution of claim 1. mixtures of alcohols and denaturants may generally be used.