Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur

Definitions

• This invention relates to articles suitable for oral and personal hygiene use and comprised of polymeric material wherein the articles have bonded to the surface thereof one or more chemically or biologically active agent(s).
• suitable articles include eye glasses, contact lens, toothbrushes, tooth picks, dentures, dental floss, razors, hair brushes and combs.
• the polymeric material is selected from the group consisting of polyamides, polystyrenes, styrene- acrylonitrile copolymers, acrylonitrile-butadiene-styrene copolymers, polyacrylates, polyesters and polypropylenes; preferably nylon and cellulose acetate propionate.
• the active agent preferably is a quaternary ammonium compound, such as 3-(trimethoxysilyl) propyldimethyloctadecyl ammonium chloride.
• This invention also relates to a method for applying a coating of chemically or biologically active agent(s) to an oral or personal hygiene article comprised of polymeric material by (a) directly permanently bonding said active agent to the surface of said article, or (b) (1) contacting said articles with an acid, alkaline hydroxide or organic solvent and (2) subsequently permanently bonding said active agent(s) to the surface of said article.
• the invention yields oral and personal hygiene articles which have anti-bacterial and/or anti-microbial coatings and/or coatings of active agents useful in retarding or preventing plaque, gingivitis, periodontitis, tooth and gum pain and diseases and infections of the skin, hair, scalp and eyes.
• anti-bacterial and/or anti-microbial coatings and/or coatings of active agents useful in retarding or preventing plaque, gingivitis, periodontitis, tooth and gum pain and diseases and infections of the skin, hair, scalp and eyes.
• toothbrushes, hair brushes and combs can be a haven for bacterial and/or microbial growth
• oral and personal hygiene articles _ which have one or more active agents bonded to the surface thereof.
• oral and personal hygiene articles * which possess permanent or long-lasting anti-bacterial and/or anti-microbial activity.
• US Patent No. 4,866,192 describes organosilicone quaternary ammonium antimicrobial compounds to treat rayon fabric and other surfaces.
• US Patent No. 4,371,577 describes antimicrobial carpet which has been treated with an amino acid type surfactant and an organosilicone quaternary ammonium salt.
• US Patent No. 4,621,120 describes antibacterial compositions comprising vinyl copolymers having quaternary nitrogen groups. These compositions are disclosed as being useful in mouthwashes, toothpastes and dental creams.
• US Patent No. 3,170,901 describes quaternary ammonium compounds and polymers thereof which are useful in treating paper and textile fabrics for imparting , , to shrinkage.
• US Patent No. 4,025,617 describes antimicrobial quaternary ⁇ ammonium copolymers formed by the condensation of at least two di-functional tertiary amines and l,4-dihalo-2-butene. These copolymers are described as being useful for the antimicrobial treatment of circulatory and standing waters.
• US Patent No. 4,482,680 discloses poly(vinylbenzyl quaternary ammonium) halides which are useful as preservatives for cosmetic and pharmaceutical compositions and as disinfectant cleansers.
• US Patent No. 4,161,518 describes dentifrice compositions containing a quaternary ammonium organosilicone.
• US Patent No. 4,394,378 describes certain silyl quaternary ammonium salts, such as 3-(trimethoxylsilyl) propyldidecylmethyl ammonium chloride, which is useful for antimicrobial treatment of textile fibers, siliceous- materials, metals, leather, wood and plastics.
• US Patent No. 4,161,518 describes dentifrice compositions containing a quaternary ammonium organosiloxane which is useful in inhibiting plaque formation on teeth.
• US Patent No. 4,615,937 describes antimicrobially-active web and wet wipes containing an organosilicone quaternary ammonium salt.
• US Patent No. 4,721,511 describes antimicrobial fabrics having a bioactive amount of a silicone quaternary amine.
• US Patent No. 4,282,366 describes natural and synthetic fabrics impregnated with organosilicone quaternary ammonium compounds as antimicrobial agents.
• a method for preparing antimicrobial foams containing quaternary ammonium salts of silanes is described in US Patent No. 4,631,297.
• US Patent No. 4,408,996 describes a process for dying bioactive cellulosic fabrics by applying a mixture of organosilicone polymer, a dye and a silyl quaternary amine.
• US Patent No. 3,730,701 describes a method for controlling the growth of algae in water by adding certain silyl quaternary amines.
• US Patent No. 4,847,088 describes synergistic antimicrobial compositions comprising a quaternary ammonium compound and an acid which are useful in treating carpets, fabrics, walls and furnishings.
• the present invention relates to personal and oral hygiene products which have been treated to bond active agent(s)to their surfaces.
• the present invention involves an article comprised of polymeric material having bonded to the surface thereof one or more chemically or biologically active agent(s), wherein said article is suitable for oral or personal hygiene use, and said active agent is substantially non-leachable from the surface of said article in a water-based medium.
• Articles covered by this invention include any article of manufacture which is suitable for oral or personal hygiene use.
• Oral hygiene as used herein means useful for cleaning and caring for the teeth, gums, dentures or any other parts of the oral cavity.
• Personal hygiene as used herein means useful for cleaning and caring for the hair, scalp, skin, ears, nose, eyes and other parts of the face and head.
• Preferred articles within the scope of this invention include a toothbrush, dental floss, toothpick, comb, hair brush, razor, eyeglass lens and frames and contact lens.
• Suitable articles according to this invention may be composed partly or entirely of a polymeric material or have an exterior surface comprised of a polymeric material.
• the polymeric material can be a natural or synthetic polymer.
• the polymeric material preferably is polyamides, polyacrylates, polyesters, polypropylenes, polystyrenes, styrene-acryl-onitrile copolymers, acrylonitrile-butadien-
• estyrene copolymers cellulose esters and blends and combinations thereof.
• the most preferred polymeric materials are nylon and cellulose acetate propionate.
• An essential feature of this invention is that the article has permanently bonded to the polymeric surface thereof one or more chemically or biologically active agent(s). These active agent(s) are bonded to the polymeric surfaces of the article, such that the agent(s) are substantially non-leachable from the surface of said article in a water-based medium.
• Suitable active agents would include any compound(s) having antimicrobial activity and which are capable of being bonded to the polymeric surfaces of the article.
• Preferred active agents include the quaternary ammonium compounds, organosilicone quaternary ammonium compounds, cetyl pyridinium compounds, guanidine compounds, bis-guanidine compounds and isothiouronium halide compounds.
• Preferred quaternary ammonium compounds useful for this invention have the formula:
• I.. is CH_-phenyl or an alkyl group containing about 8-22 carbon atoms
• R_ is methyl, ethyl, or an alkyl group containing about 8-22 carbon atoms
• R 3 is methyl or ethyl
• R. is an alkyl group containing about 1-6 carbon atoms
• X is an anion
• Y is a group having the structure:
• R. wherein R. , R restroom, and R_ are as described above, X is an anion and n is an integer from about 1-6 (preferably
• organosilicone quaternary ammonium compounds are n-octadecyldimethyl[3-(trimethoxysilyl)propyl] ammonium chloride, n-tetradecyldimethyl [3-(trimethoxysilyl) propyl] ammonium chloride, n-decyldimethyl[3-(trimethoxy- silyl) ropyl] ammonium chloride, n-didodecylmethyl[3-(tri- methoxysilyl)propyl] ammonium chloride, and n-dodecyldi- methyl[3-(trimethoxysilyl)propyl] ammonium chloride.
• active agents can include the nitrogen as part of a heterocyclic system, such as a cetyl pyridiniu compound.
• a cetyl pyridiniu compound is the preferred cetyl pyridinium compound.
• the isothiouronium halide compounds are also suitable for use as active agents according to this invention.
• the preferred isothiouronium halide compound for use in this invention is (trimeth ⁇ xysilylpropyl) isothiouronium chloride.
• the articles of this invention have the active agent(s) bonded to the polymeric surfaces of the articles, such that the active agent(s) is permanently attached to the articles.
• the articles must have the active age ⁇ t(s) bonded to the polymeric surfaces thereof such that the agent(s) is substantially non-leachable in an aqueous medium.
• the articles have a polymeric surface which has permanent antibacterial and/or antimicrobial activity which can not be leached out by saliva, shampoos, shaving creams, toothpastes and other aqueous-containing mediums.
• the active agents can be permanently attached to the polymeric surfaces of the articles by any suitable means, such as chemical linking using multifunctional reactive * organics (such as bis-carbenes or bis-nitrenes), silane coupling systems, plasma activation, flame activation, chemical treatment and other polymer grafting techniques.
• suitable means such as chemical linking using multifunctional reactive * organics (such as bis-carbenes or bis-nitrenes), silane coupling systems, plasma activation, flame activation, chemical treatment and other polymer grafting techniques.
• the preferred attachment mechanism is a silane coupling system. It is believed, although Applicant does not intend to be limited thereby, that the alkoxysilyl end of the active agent is hydrolyzed to the corresponding hydroxy component in the presence of water.
• the active agent can be bonded to the polymeric surface of the article by any type of bonding, it is preferred that the agent be covalently bonded to the polymeric surface of the article.
• the present invention also includes a method for applying a coating of chemically or biologically active agent to an oral or personal hygiene article comprised of polymeric material.
• This method can involve permanently bond ng the active agent directly to the untreated surface of the article.
• the method can also comprise the steps of:
• the invention also includes articles which have been treated by the above methods.
• the polymeric surface of the article has greater than about 2% of the surface area containing active sites for bonding of the active agent; more preferably greater than about 5%.
• suitable solvents for treating the polymeric surfaces of the article include any material which would expose or form reactive -OH, amide, or other reactive sites on the polymeric surfaces for bonding of the active agents.
• suitable solvents include aqueous-based organic and inorganic acids, aqueous-based alkaline hydroxides and organic solvents.
• the preferred acids are sulfuric and acetic acid.
• the preferred alkaline hydroxides are potassium hydroxide and sodium hydroxide.
• Preferred organic solvents include methanol, ethanol, isopropanol, acetone and ethyl acetate.
• the polymeric surfaces of the articles are contacted with the solvent for a sufficient time ranging anywhere from a few minutes to several hours. The solvents can be used alone, in combination or sequentially.
• the article can be contacted with the active agent for a sufficient time for the active agent to bond to the surface.
• the active agent is in a solution of water or other suitable solvent.
• the solution can contain the active agent in any concentration, but preferably contains from about 1% to about 4% wt./vol. of the active agent.
• the article can be dried, rinsed and cured at an elevated temperature (preferably about 50-125°C) .
• the drying and curing conditions,such as temperature, time and humidity, should be selected such that the dimensional stability of the article is not adversely affected.
• the articles of this invention are effective against a wide variety of microbial species, and they continuously inhibit the growth of microbial organisms on the surface thereof.
• the articles have demonstrated antimicrobial activity against Candida albicans,
• Various treatment solutions were prepared within the scope of this invention containing 1%, 2% and 4% wt./vol., respectively, of the active agent.
• Each solution was prepared by mixing 10 ml. of concentrated acetic acid and 2 grams of surfactant (Zonyl FSN from DuPont Co.) with deionized water, followed by either 10, 10 20 or 40 grams of the active agent, to make one liter of each solution. The solution is agitated for about 30 minutes to hydrolyze the active agent.
• surfactant Zonyl FSN from DuPont Co.
• Nylon toothbrush bristle fibers were treated with the solutions of samples 1-3 by agitating the bristles in the respective solutions for about 30 minutes.
• the bristle fibers were removed from the solutions and dried at ambient conditions for about 3 hours.
• the fibers were then rinsed with deionized water and heated in an oven for about 10 minutes at about 125°C.
• the fibers were cooled at room temperature and the samples were place in inocula of Staphylococcus aureus, Pseudomonas aeruginosa and Candida albicans, respectively. The fibers were then removed from the inocula.
• toothbrush heads comprised of cellulose acetate propionate were treated with the solutions of Samples 1-3 and evaluated for antimicrobial activity. The results are presented in Table III below.
• toothbrush heads comprised of cellulose acetate propionate were treated with the solutions of samples 4-6 and evaluated for antimicrobial activity. The results are present in Table IV below.
• toothbrush heads comprised of cellulose acetate propionate were treated with the solutions of Samples 7-9 and evaluated for antimicrobial activity. The results are presented in Table V below.
• toothbrush heads comprised of cellulose acetate propionate were treated with the solutions of Samples 10-12 and evaluated for antimicrobial activity. The results are presented in Table VI below.
• Toothbrush heads comprised of cellulose acetate propionate,and treated with the solution of Sample 3 according to the procedures of Example II, were evaluated for leachability of the active agent. Some of these 3 treated toothbrush heads were washed several times with water, while others were unwashed.
• the washed and unwashed toothbrush heads were evaluated for leachability using a bromophenol blue colorimetric analytical method.
• a bromophenol blue 10 solution was prepared by mixing 0.1125 grams bromophenol blue, 450 grams of deionized water and 0.75 ml. of 10% a 2 C0 3 .
• Two of the washed toothbrush heads were placed in a 4-ounce french square bottle along with 50 ml. of

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• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Environmental Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Zoology (AREA)
• Plant Pathology (AREA)
• Toxicology (AREA)
• Cosmetics (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Detergent Compositions (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Brushes (AREA)

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• 1991
  • 1991-12-05 JP JP4505234A patent/JPH06506197A/ja active Pending
  • 1991-12-05 AU AU12598/92A patent/AU1259892A/en not_active Abandoned
  • 1991-12-05 WO PCT/US1991/009116 patent/WO1992015198A1/en not_active Application Discontinuation
  • 1991-12-05 BR BR9107297A patent/BR9107297A/pt unknown
  • 1991-12-05 CA CA002104462A patent/CA2104462A1/en not_active Abandoned
• 1992
  • 1992-02-28 MX MX9200893A patent/MX9200893A/es unknown
  • 1992-02-28 ZA ZA921537A patent/ZA921537B/xx unknown
  • 1992-02-28 NZ NZ241780A patent/NZ241780A/en unknown
  • 1992-09-19 EP EP92904862A patent/EP0586384A1/en not_active Withdrawn

Non-Patent Citations (1)

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