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WO2002030364A1 - Compositions adhesives pour prothese dentaire - Google Patents

Compositions adhesives pour prothese dentaire Download PDF

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Publication number
WO2002030364A1
WO2002030364A1 PCT/US2001/031741 US0131741W WO0230364A1 WO 2002030364 A1 WO2002030364 A1 WO 2002030364A1 US 0131741 W US0131741 W US 0131741W WO 0230364 A1 WO0230364 A1 WO 0230364A1
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WO
WIPO (PCT)
Prior art keywords
denture adhesive
base composition
adhesive base
composition
mixtures
Prior art date
Application number
PCT/US2001/031741
Other languages
English (en)
Inventor
Rajeshwari Patel
Alan A Halecky
Original Assignee
Block Drug Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Block Drug Company filed Critical Block Drug Company
Priority to AU2001296801A priority Critical patent/AU2001296801A1/en
Priority to US10/398,850 priority patent/US20040034120A1/en
Publication of WO2002030364A1 publication Critical patent/WO2002030364A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins

Definitions

  • the present invention is directed to denture adhesives or stabilizers, and particularly to an improved denture adhesive composition.
  • adherent powders prepared from natural gum materials such as karaya, acacia or tragacanth gum. These materials have the property of swelling to many times their original volume upon the addition of water to form a gelatinous or mucilaginous mass. Cream forms of the adherent, prepared from finely ground particles of the gums, were also available and used instead of the powder compositions.
  • U.S. Patent No. 2,978,812 discloses a denture fixative composition which includes an ethylene oxide polymer having a molecular weight between 50,000 and 5,000,000 in an amount preferably comprising at least 50% of the active fixative material.
  • ethylene oxide polymer or PEO
  • PEO ethylene oxide polymer
  • U.S. Patent No. 3,003,988 describes the use of mixed salts of more than 40 wt.% of a water-insoluble water-sensitized polymeric material consisting essentially of lower alkyl vinyl ether maleic anhydride polymers.
  • U.S. Patent No. 5,001,170 discloses a substantially anhydrous mixture of about 20-40 wt.% of methyl vinyl ether maleic acid copolymer, 20-40 wt.% of PVP, and 20-40 wt % of ethylene oxide polymer.
  • Recent improvements include the use of a lower alkyl vinyl ether maleic acid, anhydride, or salt polymer or mixtures thereof and one or more metallic salts selected from the group consisting of calcium, magnesium, strontium, sodium, potassium, zirconium, and zinc, or mixtures thereof.
  • U.S. Patent No. 5,073,604 discloses a denture adhesive composition with mixed partial salts of a lower alkyl vinyl ether maleic acid copolymer, wherein said partial salts contain as the cationic salt function, (a) from about 10% to about 65% zinc or strontium cations; and (b) from about 10% to about 75% calcium cations of the total initial carboxyl groups reacted.
  • Multi-carboxylic acids and salts thereof are commonly used in the making of disposable diapers and incontinence pads.
  • U.S. Patent No. 3,707,148 describes the use of carboxylic acids to inhibit microbial growth and ammonia formation in diapers.
  • U.S. Patent No. 3,964,486 discloses the use of adipic acid and, optionally, an effective amount of sodium adipate in diapers.
  • U.S. Patent No. 6,010,971 discloses a thermoplastic composition comprising a mixture of a PEO and a multi-carboxylic acid for use in disposable absorbent products and non- woven fibers.
  • a denture adhesive formulation comprising a denture effective amount of PEO and a multi-carboxylic acid or salt, or mixtures thereof.
  • the composition comprises from about 1 to 30 wt.% of a multi-carboxylic acid or salt, or mixtures thereof, and from about 5 to 90 wt% PEO.
  • the composition comprises from about 5 to 15 wt% of a multi-carboxylic acid or salt, or mixtures thereof, and from about 25 to 50 wt% PEO.
  • the composition comprises from about 5 to 15 wt% of a multi-carboxylic acid or salt or mixtures thereof and from about 30 to 90 wt% PEO.
  • the invention also relates to a method for adhering a denture to the oral mucosa resulting from the use of the new composition of the present invention.
  • FIGURE 1 is a graph of adhesive force in lbs. vs. the hydration time in minutes, comparing the adhesive composition of the invention with other formulations.
  • the first component of the adhesive formulation is PEO.
  • PEOs are water soluble, non-ionic, polyether homopolymers having molecular weights from about 100,000 to about 5,000,000. The homopolymers are white powders which when hydrated develop into a gelatinous mass having adhesive characteristics.
  • the polyether polymers have the chemical structure — (CH 2 CH 2 o) n - wherein n represents the degree of polymerization of the polymer and may have a value from about 2,000 to about 100,000.
  • PEOs of the type employed in the present invention are more fully described in "Poly ox" 1978, published by Union Carbide Corporation, New York, N.Y., as Technical Bulletin F-44029B.
  • PEOs useful in the invention include linear, water- soluble PEOs, as well as cross-linked PEOs. PEOs are commercially available from Union Carbide Corporation under the tradename POLYOX.
  • a multi-carboxylic acid is any acid that comprises two or more carboxylic acid groups, and preferably oligomers and polymers containing three or more carboxylic groups.
  • Suitable for use in the present invention are dicarboxylic acids, which comprise two carboxylic acid groups.
  • Suitable multi-carboxylic acids include, but are not limited to, glutaric, adipic acid, sebacic acid, malonic acid, citric acid, succinic acid, pimelic acid, suberic acid, azelaic acid, and mixtures thereof.
  • the multi-carboxylic acids suitable for use in the present invention are generally water-soluble but generally exhibit a solubility that is relatively slower than that exhibited by PEO. As such, the adding of the multi-carboxylic acid to a PEO generally reduces or slows down the water-solubility of the overall mixture.
  • the multi-carboxylic acid used is adipic acid, which is widely available in commercial quantities.
  • Adipic acid has acid groups that are six carbons apart (inclusive of the carbonyl carbon).
  • the acid is prepared by oxidizing cyclohexanol with concentrated nitric acid.
  • sodium adipate is used.
  • the above two components, PEO and multi-carboxylic acid or salt are used in safe and adhesively effective amounts, which herein means an amount sufficient to provide adherence to the oral cavity.
  • the composition comprises from about 5 to 90 wt% PEO and about 1 to 30 wt.% of a multi-carboxylic acid or salt, or mixtures thereof.
  • the denture adhesive composition comprises from about 1 to 15 wt.% of a multi-carboxylic acid or salt, or mixtures thereof, and from about 25 to 50 wt.% PEO.
  • the denture adhesive composition comprises from about 5 to 15 wt.% of a multi-carboxylic acid or salt, or mixtures thereof, and from about 35 to 50 wt % PEO.
  • the composition comprises from about 1 to 15 wt.% of a multi-carboxylic acid, or salt, or mixtures thereof, and 30 to 90 wt.% PEO.
  • the composition may optionally contain other components to aid in enhancing the adhesive nature of the base components, including those commonly known and used in the dental adhesive art.
  • Methyl vinyl ether maleic- acid, anhydride, or salts of the copolymers within, and equivalents thereof, may be included although it is not necessary to do so.
  • Suitable optional adhesive components include the traditional water-soluble hydrophilic colloids or polymers having the property of swelling upon exposure to moisture to form a mucilaginous mass. These materials include copolymers of maleic acid or maleic anhydride or salts thereof, natural gums, synthetic polymeric gums, synthetic polymers, mucoadhesive polymers, hydrophilic polymers, saccharide derivatives, cellulose derivatives, and mixtures thereof.
  • Examples of such materials include karaya gum, guar gum, gelatin, algin, sodium alginate, tragacanth, chitosan, acrylamide polymers, polyacrylic acid derivatives sold under the trademark Carbopol®, polyvinyl alcohol, polyamines, polyquarternary compounds, polybutenes, silicones, cationic polyacrylamide polymers.
  • the optional adhesive components are cellulose derivatives, or salts thereof, such as methylcellulose, sodium carboxymethyl cellulose, hydroxyethyl cellulose, hydropropyl cellulose, hydroxypropylmethyl cellulose, carboxymethyl cellulose.
  • the optional components are carboxy-methylcellulose, karaya gum, sodium alginate, chitosan, polyvinyl alcohol, and mixtures thereof.
  • the other adhesive components may be present at a level of from about 0 to about 70 wt.%. In one embodiment, they are from about 5 to about 50 wt.%. In another embodiment, they are from about 2 to about 20 wt.%.
  • the denture adhesive composition may be formulated with additional components well known in the denture adhesive art including waxes, oils, preservatives, flavoring agents, colorants, sweetening agents, viscosity modifiers, and so forth.
  • the waxes useful in the invention include without limitation, both natural and synthetic waxes and include without limitation animal waxes such as beeswax, lanolin and shellac wax, vegetable waxes such as carnauba, candelilla and bayberry wax, mineral wax such as petroleum waxes including paraffin, and microcrystalline.
  • the oils useful in the invention include without limitation, mineral oil, vegetable oil such as corn, soybean, cottonseed, castor, palm and coconut oils and animal oil such as fish oil, and oleic acid.
  • Flavoring agents well known to the denture adhesive art may be added to the compositions of the present invention.
  • These flavoring agents include without limitation, synthetic flavor oils and/or oils derived from plants, leaves, flowers, fruits and so forth, and combinations thereof.
  • Representative flavor oils include, spearmint oil, cinnamon oil, oil of wintergreen (methylsalicylate) and peppermint oils.
  • artificial, natural or synthetic fruit flavors such as citrus oil including lemon, orange, grape, lime, and grapefruit, and fruit essences including apple, strawberry, cherry, pineapple, and so forth.
  • the flavoring agent may be a liquid, spray dried, encapsulated, or absorbed on a carrier, and mixtures thereof.
  • a preferred flavoring agent is peppermint oil.
  • the amount of flavoring agent utilized varies depending on such factors as flavor type, adhesive formulation and strength desired. In general, amounts of about 0.01 to about 5.0 wt.% of the total denture adhesive composition are suitable. In one embodiment of the invention, an amount of about 0.05 to 0.15 wt.% is used.
  • Preservatives which may be used in the denture adhesive formulations of the invention include those known antimicrobial agents conventionally employed in the art, such as benzoic acid and sodium benzoate; the parabens; sorbic acid and sorbates; propionic acid and propionates; acetic acid and acetates; nitrates and nitrites; sulfur dioxide and sulfites; antibiotics; diethyl pyrocarbonate; epoxides; hydrogen peroxide; and phosphates.
  • the parabens include the methyl, ethyl, propyl, and butyl esters of parahydroxybenzoic acid. Methyl paraben and propyl paraben are the preferred preservatives of the invention, utilized in amounts of about 0.03 to about 0.06 wt.% of the total denture adhesive composition.
  • the denture adhesive compositions may also include the use of sweeteners well known in the art.
  • the sweetening agent may be selected from a wide range of materials including water-soluble agents, water-soluble artificial sweeteners, and dipeptide based sweeteners, including mixtures thereof.
  • sweeteners include without limitation, (a) water-soluble sweetening agents such as monosaccharides, disaccharides and polysaccharides such as xylose, ribose, glucose, mannose, galactose, fructose, dextrose, sucrose, sugar, maltose, partially hydrolyzed starch, or corn syrup solids and sugar alcohols such as sorbitol, xylitol, mannitol, maltitol, hydrogenated starch hydrolysate, and mixtures thereof; (b) water-soluble artificial sweeteners such as the soluble saccharin salts, i.e., sodium or calcium saccharin salts, cyclamate salts, acesulfam-K, sucralose, and the like, and the free acid form of saccharin; and (c) dipeptide based sweeteners such as L-aspartyl-L-phenylalanine methyl ester, and the like. In general, the amount of sweetener may
  • the colorants useful in the present invention include the pigments such as titanium dioxide, and may also include dyes suitable for food, drug and cosmetic applications. These colorants are known as FD&C dyes. Illustrative examples include without limitation, indigo dye, known as FD&C Blue No. 2, which is the disodium salt of 5,5 -indigotindi-sulfonic acid; FD&C Green No. 1, comprising a triphenylmethylene dye and is the monosodium salt of the 4-[4-N-ethyl-p-sulfobenzylamino) diphenylmethylene]-[l-(N-ethyl-N-P-sulfobenzyl)-2,5-cyclohexadienimine]. A preferred colorant is FD&C Red No. 3.
  • the viscosity modifiers useful herein include without limitation, quaternary ammonium compounds and similar agents, starches, gums, casein, gelatin and semi- synthetic cellulose.
  • composition of the present invention may also be used as a denture adhesive and/or bioadhesive and comprise one or more therapeutic actives suitable for mucosal or topical administration.
  • suitable for mucosal or topical administration describes agents which are pharmacologically active when absorbed through internal mucosal surfaces of the body such as the oral cavity, or applied to the surfaces of the skin.
  • Therapeutic actives may be present at a level from about 0 to about 40 wt.% of the composition.
  • Therapeutic actives that are useful in the instant compositions include antimicrobial agents such as iodine, sulfonamides, bisbiguanides, or phenolics; antibiotics such as tetracycline, neomycin, kanamycin, metronidazole, or clindamycin; anti-inflammatory agents such as aspirin, acetaminophen, naproxen and its salts, ibuprofen, ketorolac, flurbiprofen, indomethacin, eugenol, or hydrocortisone; dentinal desensitizing agents such as potassium nitrate, potassium chloride, strontium chloride or sodium fluoride; anesthetic agents such as lidocaine or benzocaine; antifungals; aromatics such as camphor, eucalyptus oil, and aldehyde derivatives such as benzaldehyde; insulin; steriods; and anti-neoplasties. It is recognized that
  • the denture adhesive compositions may be in the form of a powder, a paste, a cream, or a liner.
  • Means for preparing such formulations is well known in the denture adhesive art, employing conventional types of mixing equipment for blending, heating, and cooling solids and liquids. In one embodiment, mixing is performed at temperatures suitable to melt the components, e.g., petrolatum, to be blended.
  • the components are admixed with flavoring agents and colorants, together with other ingredients such as non-toxic anti-caking agents (silica, magnesium stearate, talcum powder, and the like).
  • non-toxic anti-caking agents sica, magnesium stearate, talcum powder, and the like.
  • the mixture of ingredients is thoroughly agitated or stirred to yield a generally homogenous intermixing of all components.
  • the components are admixed with petrolatum along with the previously described waxes, oils, preservatives, flavoring agents, colorants, sweetening agents, viscosity modifiers, and so forth.
  • the component are uniformly mixed and then coated onto a non-adhesive self supporting coating layer by any conventional coating techniques, such as by spraying (if the material is liquid or slurry or dissolved or suspended in a liquid such as water) or by sifting (if the denture adhesive is in powder form).
  • the components are admixed with the previously described waxes, oils, preservatives, flavoring agents, colorants, sweetening agents, viscosity modifiers, and so forth.
  • the liner is then formed by any variety of techniques known in the polymer film-forming art, including casting, calendaring, coating, and extrusion.
  • the components are first mechanically softened by a ring roller; smoothed on a hydraulic press, and die-cut as desired into denture liner shapes or other desired shapes.
  • a ring roller smoothed on a hydraulic press, and die-cut as desired into denture liner shapes or other desired shapes.
  • Example 1 Cream Formulation
  • PEO and sodium adipate were mixed together and added to the melted petrolatum and mineral oil in a KitchenAid mixer with stirring. Flavors, dyes and other optional ingredients were added and intimately mixed in for about 30 minutes.
  • the resultant denture adhesive composition was a viscous material which turned into a smooth soft mass upon wetting and mixing with water or saliva.
  • PEO powder was first admixed with sodium adipate in a KitchenAidTM mixer and then added to a mixture of CMC and HPMC. The blend was plasticized with an appropriate amount of water and glycerin and extruded forming a film.
  • a typical denture liner formulation is as follows:
  • HPMC Hydropropylmethyl cellulose 12.50
  • Example 3 Powder Formulation For this formulation, PEO powder was mixed with sodium adipate and other ingredients in a blender.
  • a typical denture powder formulation is as follows: Sodium Adipate 5.00
  • PEO was added to melted petrolatum and mineral oil in a KitchenAidTM mixer with stirring. Flavors, dyes and other optional ingredients may be added in the next mixing phase and intimately mixed in for about 30 minutes.
  • the resultant denture adhesive composition was a viscous material which turned into a smooth soft mass upon wetting and mixing with water or saliva.
  • Comparative Example 4 (with Polyox only and without multi-carboxylic acid/salt) and a commercially available denture adhesive cream formulation Fixodent®, known to contain metal salts of methyl vinyl ether/maleic acid or anhydride copolymers or Gantrez® as disclosed in U.S. Patent 5,073,604.
  • the samples were evaluated for adhesion characteristics by an adhesive force test called the "Dislodge Force Method.”
  • the test method involves the use of two plates, an upper and a lower plate, in a water bath at about 37°C.
  • the upper plate is lined with felt (representing the Maxilla) and attached to a Chatillon® gauge and moving ram.
  • the lower plate is made out of polymethyl methacrylate (representing the denture) and attached onto a hinge which is attached to a Chatillon® test stand.
  • the upper plate applies downward pressure, the lower plate swings downward onto the hinge. This action simulates the biting motion of the mouth.
  • the swinging motion of the lower plate simulates the dislodgement of a denture.
  • Figure 1 compares the cream formulation of the present invention (Example 1) with Comparatives Examples 4 ( Polyox only) and the commercially available denture adhesive composition, Fixodent®.
  • the adhesive force evaluation test indicated that the composition of the present invention displayed comparable, if not superior, time hold property to the commercially available denture composition containing metal salts of methyl vinyl ether/maleic acid or anhydride copolymers or Gantrez®.
  • Example 1 The denture cream formulation in Example 1 was tested against commercially available denture adhesive cream formulation Fixodent® Original, containing metallic crosslinked methy vinyl ether maleic acid copolymer. The sensory tests were carried out to evaluate the organoleptic characteristics of the PEO/multi-carboxylic acid/salt formulation of the present invention against a leading market denture adhesive.
  • organoleptic evaluation tests several expert evaluation panelists were presented with two samples of denture adhesive creams. One was the formulation of the present invention, the other was the commercial formulation. The panelists were asked to complete a questionnaire to evaluate the denture creams based on fifteen different criteria, e.g., mouth feel, hold property, time hold property develops, oozing property, ease to remove, ease to apply, etc.
  • the denture formulation of the present invention was judged to be comparable to the commercial formulations comprising metal salts of methyl vinyl ether/maleic acid or anhydride copolymers of Gantrez®. It was also found that the denture formulation of the present invention did not exhibit any objectionable phase separation or oozing from a dental plate.

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  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dental Preparations (AREA)

Abstract

L'invention concerne une composition de base adhésive pour prothèse dentaire, qui comprend un sel ou un acide multicarboxylique, ou des mélanges de ceux-ci, et un polymère d'oxyde d'éthylène. L'invention concerne également une composition adhésive comprenant cette composition de base avec d'autres composants adhésifs facultatifs. L'invention concerne également un procédé permettant de préparer une nouvelle composition de base adhésive pour prothèse dentaire comprenant un sel ou un acide multicarboxylique, ou des mélanges de ceux-ci, et un polymère d'oxyde d'éthylène.
PCT/US2001/031741 2000-10-13 2001-10-10 Compositions adhesives pour prothese dentaire WO2002030364A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2001296801A AU2001296801A1 (en) 2000-10-13 2001-10-10 Denture adhesive compositions
US10/398,850 US20040034120A1 (en) 2001-10-10 2001-10-10 Denture adhesive compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US68778000A 2000-10-13 2000-10-13
US09/687,780 2000-10-13

Publications (1)

Publication Number Publication Date
WO2002030364A1 true WO2002030364A1 (fr) 2002-04-18

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Family Applications (1)

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PCT/US2001/031741 WO2002030364A1 (fr) 2000-10-13 2001-10-10 Compositions adhesives pour prothese dentaire

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AU (1) AU2001296801A1 (fr)
WO (1) WO2002030364A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4514528A (en) * 1983-02-16 1985-04-30 Richardson-Vicks Inc. Hydrophilic denture adhesive
US5001170A (en) * 1989-12-01 1991-03-19 Warner-Lambert Company Denture stabilizer
US5302628A (en) * 1992-02-03 1994-04-12 Block Drug Company, Inc. Denture adhesive composition
US6010971A (en) * 1997-11-21 2000-01-04 Kimberly-Clark Worldwide, Inc. Polyethylene oxide thermoplastic composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4514528A (en) * 1983-02-16 1985-04-30 Richardson-Vicks Inc. Hydrophilic denture adhesive
US5001170A (en) * 1989-12-01 1991-03-19 Warner-Lambert Company Denture stabilizer
US5302628A (en) * 1992-02-03 1994-04-12 Block Drug Company, Inc. Denture adhesive composition
US6010971A (en) * 1997-11-21 2000-01-04 Kimberly-Clark Worldwide, Inc. Polyethylene oxide thermoplastic composition

Also Published As

Publication number Publication date
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