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WO1999032046A1 - Revetement pour fil dentaire en ptfe - Google Patents

Revetement pour fil dentaire en ptfe Download PDF

Info

Publication number
WO1999032046A1
WO1999032046A1 PCT/GB1998/003762 GB9803762W WO9932046A1 WO 1999032046 A1 WO1999032046 A1 WO 1999032046A1 GB 9803762 W GB9803762 W GB 9803762W WO 9932046 A1 WO9932046 A1 WO 9932046A1
Authority
WO
WIPO (PCT)
Prior art keywords
ptfe
dental floss
coating
coating material
floss
Prior art date
Application number
PCT/GB1998/003762
Other languages
English (en)
Inventor
Jacob Moses Blass
Dennis Aston
Original Assignee
Westone Products Limited
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 Westone Products Limited filed Critical Westone Products Limited
Priority to AU15708/99A priority Critical patent/AU1570899A/en
Publication of WO1999032046A1 publication Critical patent/WO1999032046A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
    • A61C15/00—Devices for cleaning between the teeth
    • A61C15/04—Dental floss; Floss holders
    • A61C15/041—Dental floss
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form

Definitions

  • the invention relates to a dental floss comprising one or more elongate PTFE elements and a coating applied to increase the coefficient of friction to improve grip properties of the PTFE material.
  • the term "dental floss” here includes dental tape .
  • dental flosses have been used for many years to clean interdental spaces and spaces under the gum margin.
  • a variety of flosses include adjuvants including medicinal compounds e.g. fluoride and bactericidal compounds to increase the effectiveness of the floss in inhibiting dental caries and flavourings to improve taste during flossing. In general these adjuvants are applied in a coating or as a coating on the floss.
  • flossing has been shown to be beneficial to oral health, inhibiting dental caries and gum problems, dental floss is considered by many consumers to be uncomfortable to use.
  • the problems in consumer acceptance of dental floss relate to its high coefficient of friction. When pulling dental floss between teeth, substantial force may need to be applied. This often results in the floss impacting on the gums, the resulting irritation of the gums often causing bleeding.
  • WO96/10478 (US patents 5657779 and 5806539) describes manufacture of a new form of PTFE which is suitable for use as a dental floss, either coated with wax or in uncoated form, by reason of its surface properties.
  • EP 335466 and WO92/10978 both also propose that additives, such as dentifrices and components having a pharmaceutical or other beneficial effect when released in the mouth, are incorporated in the dental floss. This might be done either in the wax or as a substrate coating on the PTFE before the wax is applied.
  • WO97/24078 discloses a method of incorporating additive in the PTFE material of the floss .
  • PTFE has a lower coefficient of friction than conventional materials used to make floss materials, the floss is still effective in cleaning tooth surfaces.
  • the reduced friction of coefficient of floss enables the user to insert the floss between tight interdental spaces more easily with reduced propensity for the floss to cause bleeding of the gums .
  • the extremely low coefficient of friction of PTFE floss makes the floss difficult to handle.
  • wax has been proposed to increase the coefficient of friction of the floss to enable easier grip during use. In use, the wax coating provides an increased coefficient of friction for handling.
  • the present invention aims to provide a coating for PTFE floss which results in improved properties and avoids the disadvantage of the sticky feeling of wax on the fingers of the user.
  • a dental floss in the form of an elongate article comprising one or more elongate PTFE elements providing the tensile strength of the floss.
  • a coating of a coating material which (i) is not a wax
  • the present inventors have investigated the possibility of coating of PTFE dental floss using various food quality materials such as mono-, di- and tri- glycerides of stearates and palmitates, and the acids and alcohols of C 14 to C 20 long chain aliphatic compounds. It has surprisingly been found that a class of water- insoluble materials can adhere satisfactorily to the PTFE without impairing the behaviour of the PTFE as a floss and that the coating improves grippability of the product by a user without leaving a sticky residue on the fingers.
  • the coating weight can be very small, yet provide a desired coefficient of friction.
  • the dental floss of the invention typically has, to provide its tensile strength, one or more strands which are integral, unitary PTFE elements.
  • PTFE is here used, as is usual, to describe a range of polymers based on polytetrafluoroethylene .
  • small amounts of co-monomers may be included, such as ethylene, chlorotrifluoroethylene or hexafluoropropylene, provided that the properties of the product are satisfactory.
  • PTFE is extruded with a lubricant, which is subsequently removed, for example, by heat cleaning or solvent extraction.
  • the PTFE may, as is conventional, include one or more fillers and/or pigments.
  • unfilled PTFE is preferred.
  • PTFE has been expanded by stretching in at least one direction, typically at an elevated temperature, so as to increase in porosity.
  • the resulting PTFE has a porous structure.
  • Suitable PTFE materials are described in WO96/10478 (US patents 5657779 and 5806539) .
  • a porous PTFE material is used, with a density of not more than 1.5g/cm 3 .
  • the tensile strength of the PTFE is at least 100 MPa, e.g. in the range 200 - 600 MPa.
  • the PTFE is a monofilament ribbon, and preferably the width of the ribbon is in the range 0.5 - 4mm, more preferably 1 - 3mm, most preferably 1.2 - 2.4mm.
  • the thickness is preferably in the range 20 - 120 ⁇ m, more preferably 20 - lOO ⁇ m and most preferably 40 - lOO ⁇ m.
  • the ribbon may be twisted.
  • the floss has typically a density of about 0.9g/cm 3 with typical pore size of approximately lO ⁇ m.
  • the melting point of the coating material should preferably be above normal blood temperature to avoid melting on finger contact, i.e. at least 38 ⁇ C, more preferably at least 40 °C, and preferably is in the range 42 to 62°C.
  • the PTFE element or elements are coated with coating material which (excluding any additive material which may be included as described below) is at least 90% by weight of at least one compound selected from mono-, di- and tri- glycerides of fatty acids having 14 to 20 carbon atoms, C 14 -C 20 aliphatic alcohols and C 14 -C 20 aliphatic acids. More preferably, the coating material (excluding any additive material) is at least 90% by weight of one or more compounds selected from mono-, di- and tri-glycerides of stearic, oleic and palmitic acids, stearic acid, stearyl alcohol, and cetyl alcohol .
  • the coating may consist substantially wholly of such materials (apart from any additive included) .
  • Such coatings to be used in the invention share the following common features; they are not waxes (i.e. they do not have wax characteristics, such as wide melting point range, do not exhibit softening prior to melting when heated to melting and on the floss do not have a waxy feel) ; they have relatively low melting points; the melting temperature range is narrow, e.g. not more than 10 °C, particularly not more than 6°C, preferably not more than 4°C, more preferably not more than 2'C; they are insoluble in water, they are non-toxic and preferably of food quality.
  • the narrow melting temperature range is advantageous in manufacture of the floss, because the coating when applied as a liquid just above its melting temperature can be quickly solidified, giving an even and uniform coating.
  • coatings which may be used include, but are not limited to, stearic acid, palmitic acid, glyceryl monostearate, stearyl alcohol, cetyl alcohol and hydrogenated castor oil.
  • the coating may be on one or both sides of the PTFE ribbon-shaped element.
  • the amount of the coating is preferably in the range 0.2 to 10% by weight of the dental floss, more preferably 0.2 to 5%, e.g. 1 to 5%.
  • the dental floss may include a water-soluble or water- insoluble additive material adapted to be released in the mouth in use of the floss to provide a medicinal, diagnostic, cosmetic or flavouring effect, said adjuvant material being located within the PTFE material of the PTFE element or elements and/or on the surface of said PTFE element or elements under the coating, or in the coating.
  • a suitable method of incorporating such adjuvants in the PTFE is described in WO97/24078 (US patent 5800823) .
  • melting point means the temperature of first appearance of liquid on heating.
  • the melting temperature range is the temperature range from first appearance of liquid (solidus) to disappearance of all solid (liquidus) .
  • Glyceryl monostearate is a known pharmaceutical excipient and is composed of a mixture of mono-, di-, and tri-glycerides of primarily stearic and palmitic acids. Some oleate radicals may be present . It contains not less than 90% of total fatty acid glycerides, of which at least 35% are the stearic acid monoglyceride .
  • the glyceryl monostearate used in this example had a melting point of 58 °C and a melting temperature range of about 2'C (i.e. 58 - 60"C) .
  • the glyceryl monostearate is heated to melting point and then held at about 60 °C whilst a lick roller is partially immersed in the molten mass.
  • the lick roller is driven so as to pick up a thin film of the glyceryl monostearate which is then transferred onto essentially one side only of a tape-shaped PTFE filament of dental floss dimensions which is pulled over the exposed surface of the roller.
  • the filament is wound onto bobbins for packaging in dispensers.
  • the PTFE filament was one made in accordance with WO 96/10478.
  • Glyceryl monostearate is thus applied in a suitable amount to provide the desired handling properties in use. Excessive coating may make the floss hard and brittle in use .
  • the amount of glyceryl monostearate in the coated floss is approximately 0.2 - 10% w/w, preferably 0.5 - 5% w/w (weight of glyceryl monostearate/weight of floss) .
  • the PTFE filament which is the same as used in Example 1, is treated to incorporate a flavouring by immersion batchwise in an alcohol solution of dental mint flavour.
  • the immersion may be done in a continuous process with the coating, but in either case the alcohol is allowed to evaporate before coating.
  • the flavour may also be incorporated into the filament without the use of alcohol.
  • the level of flavouring is 1 - 50%, preferably 3 - 10%, in the filament.
  • the PTFE fibre is then coated with glyceryl monostearate in the same manner as in Example 1.
  • the filament is coated with glyceryl monostearate at 0.5 - 5% w/w.
  • the glyceryl monostearate used has a narrow melting temperature range of about 2°C.
  • the product exhibits only a small amount of odour in comparison to the quantity of flavour added but, on use in the mouth, the flavour is intensified. This indicates that the flavour is essentially present in the pores of the PTFE filament and is shielded by the coating on one side. As the coating is insoluble in water this suggests that the coating is being mechanically removed from the surface of the PTFE floss during use. It may be that the flavour is released by the external force applied to the floss during use, compression of the floss forcing the flavour to migrate to the surface. Two-sided coating may be employed to give better shielding of the flavour in the PTFE.
  • active components may be incorporated, e.g. active components incorporated during manufacture of the PTFE element or incorporated in the coating.
  • active components may include, but are not limited to, fluoride-containing compounds, plaque control agents, tartar control agents, teeth whitening and bleaching agents, antibacterial agents, antifungal agents, vitamins, minerals, cooling agents e.g. menthol, colourant agents or dyes to identify plaque deposits, pharmacologically active compounds such as antibiotics, antigens, anti-inflammatory agents, analgesic agents, and haemostatic agents.
  • Example 1 is repeated with incorporation of sodium fluoride in the coating.
  • Sodium fluoride is added to the coating material in the coating bath at a level of 9% w/w. Since the sodium fluoride is not dissolved in the coating and remains suspended as discrete particles, the melting point of the coating is unaffected.
  • the amount of coating material in the coated floss is approximately 0.5 - 5% w/w.
  • the coated PTFE has been shown to release about 30% of the sodium fluoride present in the coating into water at 37 * C, thus indicating useful release into the mouth in use of the floss.
  • EXAMPLE 4 has been shown to release about 30% of the sodium fluoride present in the coating into water at 37 * C, thus indicating useful release into the mouth in use of the floss.
  • the PTFE filament which is the same as that used in Example 1, is treated in the same manner with a coating comprising a mixture of glyceryl monostearate, stearyl alcohol and sodium fluoride in the ratios 10:1:1 by weight .
  • the sodium fluoride is not dissolved in the coating.
  • the melting point of this mixture is about 58 'C.
  • the PTFE is coated with the mixture at 0.5 - 5% w/w.
  • the coated PTFE has been shown to release approximately 50% of the sodium fluoride in the coating into water at 37 ° C .
  • EXAMPLE 5 The PTFE filament, which is the same as that used in Example 1, is given a coating as described in Example
  • CPC cetylpyridinium chloride
  • the PTFE is coated with the mixture at 0.5 - 5% w/w.
  • the coated PTFE has been shown to release approximately 50% of the sodium fluoride into water at 37°C.
  • EXAMPLE 6 The PTFE filament, which is the same as that used in Example 1, is given a coating as described in Example
  • Triclosan, CPC and sodium fluoride are not dissolved in the coating, and the melting point of the coating mixture is about 58 'C.
  • the PTFE is coated at 0.5 - 5% w/w. The coated PTFE has been shown to release approximately 50% of the sodium fluoride into water at 37'C.
  • Triclosan is a water-insoluble additive but does show antibacterial action when released from the coating when the coating is mechanically removed from the filament .
  • EXAMPLE 7 The PTFE filament, which is the same as that used in Example 1, is treated in the same manner to apply a coating of stearyl alcohol containing sodium fluoride at a level of 9% w/w.
  • Stearyl alcohol has a melting point of about 58 "C and a melting point range of approximately 58 - 60 * C.
  • the PTFE is coated with the mixture at a level of 0.5 - 5% w/w.
  • Sodium fluoride is released into water at a level of approximately 50% at 37°C.
  • EXAMPLE 8 EXAMPLE 8
  • the PTFE filament is coated in the same manner with stearyl alcohol containing 5% sodium bicarbonate and 5% sodium fluoride.
  • the PTFE is coated with the mixture at 0.5 - 5% w/w.
  • the coated PTFE has been shown to release approximately 70-80% of the sodium fluoride into water at 37 'C. The same effect was obtained when silica was used instead of sodium bicarbonate.
  • the PTFE filament is coated with the mixture described in Example 8 but containing 5% CPC.
  • the PTFE is coated with the mixture at 0.5 - 5% w/w.
  • the coated PTFE has been shown to release approximately 70-80% of the sodium fluoride into water at 37"C. CPC is released into water similarly.
  • the PTFE filament is coated with the mixture described in Example 8 but containing 5% triclosan.
  • the coated PTFE has been shown to release approximately 70- 80% of the sodium fluoride into water at 37 °C.
  • the PTFE filament is treated to incorporate dental mint flavour by the processes described in Example 2.
  • the PTFE filament is then coated with stearyl alcohol which has a melting point of about 58 °C and a melting point range of 58 - 60 ° C approximately.
  • the filament is coated with stearyl alcohol at 0.5 - 5% w/w and displays properties similar to those of the product of Example 2.
  • the dental floss consisting of or comprising the PTFE tape described above, can be packaged in a conventional manner, for example in a container such as a plastics material box, with an outlet aperture through which the tape can be pulled.
  • the tape can be packed loosely in the box, or wound on a spool in the box.
  • the box may have a cutting means for assisting the breaking of the floss, and this may be a notch.
  • the PTFE tape can be used as a floss element in a flossing device, e.g. of the type where the floss element extends between two holding arms of a frame.
  • a flossing device e.g. of the type where the floss element extends between two holding arms of a frame.
  • the preferred dimensions of the bobbins containing the coated PTFE tape used as dental floss are: product contents 45m, diameter up to 26mm and depth up to 10mm.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Dentistry (AREA)
  • Birds (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne un fil dentaire sous forme de produit allongé comprenant au moins un élément allongé en PTFE assurant la résistance à la traction du fil. L'élément en PTFE est revêtu d'un matériau (i) qui n'est pas une cire, (ii) qui est solide à température ambiante (25° C), (iii) qui est insoluble dans l'eau, (iv) qui a une faible plage de fusion (par exemple moins de 10° C), (v) qui est non toxique. Le dit matériau peut comprendre, en poids, au moins 90 % d'au moins un composé choisi dans le groupe des mono-, di et triglycérides d'acides gras ayant entre 14 et 20 atomes de carbone, des alcools aliphatiques C14-C20 et des acides aliphatiques C14-C20. Ce matériau peut contenir un additif à effet aromatisant ou médicinal.
PCT/GB1998/003762 1997-12-19 1998-12-15 Revetement pour fil dentaire en ptfe WO1999032046A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU15708/99A AU1570899A (en) 1997-12-19 1998-12-15 Coating of ptfe dental floss

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9726909.6 1997-12-19
GBGB9726909.6A GB9726909D0 (en) 1997-12-19 1997-12-19 Coating of PTFE dental floss

Publications (1)

Publication Number Publication Date
WO1999032046A1 true WO1999032046A1 (fr) 1999-07-01

Family

ID=10823935

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1998/003762 WO1999032046A1 (fr) 1997-12-19 1998-12-15 Revetement pour fil dentaire en ptfe

Country Status (3)

Country Link
AU (1) AU1570899A (fr)
GB (1) GB9726909D0 (fr)
WO (1) WO1999032046A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001044420A3 (fr) * 1999-12-17 2002-07-04 Archer Daniels Midland Co Cires a base d'huiles glycerides
WO2002053059A3 (fr) * 2000-12-29 2003-05-15 Kimberly Clark Co Fil de soie dentaire et ruban dentaire enduits d'hemostatique
WO2011097623A1 (fr) * 2010-02-08 2011-08-11 The Procter & Gamble Company Fil dentaire revêtu à variabilité réduite
WO2016084862A1 (fr) * 2014-11-28 2016-06-02 旭硝子株式会社 Compositions de caoutchouc fluoré et article en caoutchouc fluoré réticulé
WO2019213298A1 (fr) * 2018-05-01 2019-11-07 Texas Tech University System Fil dentaire à revêtement médicinal adaptable pour le traitement d'une maladie des gencives

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3953566A (en) 1970-05-21 1976-04-27 W. L. Gore & Associates, Inc. Process for producing porous products
US3962153A (en) 1970-05-21 1976-06-08 W. L. Gore & Associates, Inc. Very highly stretched polytetrafluoroethylene and process therefor
EP0335466A2 (fr) 1988-03-29 1989-10-04 Colgate-Palmolive Company Soie dentaire
EP0423541A2 (fr) * 1989-10-16 1991-04-24 Colgate-Palmolive Company Articles thérapeutiques à base de polytétrafluoroéthylène
WO1992010978A1 (fr) 1990-12-20 1992-07-09 Westone Products Limited Fil dentaire et son procede de fabrication
GB2258402A (en) * 1991-07-11 1993-02-10 Colgate Palmolive Co Coated ptfe dental floss
WO1996010478A1 (fr) 1994-10-03 1996-04-11 Westone Products Limited Procede et machine permettant d'obtenir du ptfe de forme allongee, et ptfe allonge utilise notamment comme soie dentaire
WO1997024078A1 (fr) 1995-12-27 1997-07-10 Caredent Limited Elements allonges en ptfe et articles obtenus a partir de ces elements
US5665333A (en) * 1995-01-17 1997-09-09 Homola; Andrew M. Methods, compositions, and dental delivery systems for the protection of the surfaces of teeth

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3953566A (en) 1970-05-21 1976-04-27 W. L. Gore & Associates, Inc. Process for producing porous products
US3962153A (en) 1970-05-21 1976-06-08 W. L. Gore & Associates, Inc. Very highly stretched polytetrafluoroethylene and process therefor
EP0335466A2 (fr) 1988-03-29 1989-10-04 Colgate-Palmolive Company Soie dentaire
EP0423541A2 (fr) * 1989-10-16 1991-04-24 Colgate-Palmolive Company Articles thérapeutiques à base de polytétrafluoroéthylène
WO1992010978A1 (fr) 1990-12-20 1992-07-09 Westone Products Limited Fil dentaire et son procede de fabrication
GB2258402A (en) * 1991-07-11 1993-02-10 Colgate Palmolive Co Coated ptfe dental floss
WO1996010478A1 (fr) 1994-10-03 1996-04-11 Westone Products Limited Procede et machine permettant d'obtenir du ptfe de forme allongee, et ptfe allonge utilise notamment comme soie dentaire
US5657779A (en) 1994-10-03 1997-08-19 Westone Products Limited Method and apparatus for forming elongate PTFE material and PTFE material particularly dental floss
US5806539A (en) 1994-10-03 1998-09-15 Westone Products Limited Method and apparatus for forming elongate PTFE material and PTFE material particularly dental floss
US5665333A (en) * 1995-01-17 1997-09-09 Homola; Andrew M. Methods, compositions, and dental delivery systems for the protection of the surfaces of teeth
WO1997024078A1 (fr) 1995-12-27 1997-07-10 Caredent Limited Elements allonges en ptfe et articles obtenus a partir de ces elements

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001044420A3 (fr) * 1999-12-17 2002-07-04 Archer Daniels Midland Co Cires a base d'huiles glycerides
WO2002053059A3 (fr) * 2000-12-29 2003-05-15 Kimberly Clark Co Fil de soie dentaire et ruban dentaire enduits d'hemostatique
AU2002231216B2 (en) * 2000-12-29 2006-03-02 Kimberly-Clark Worldwide, Inc. Hemostat coated dental floss and hemostat coated dental tape
WO2011097623A1 (fr) * 2010-02-08 2011-08-11 The Procter & Gamble Company Fil dentaire revêtu à variabilité réduite
AU2011213605B2 (en) * 2010-02-08 2014-04-24 The Procter & Gamble Company Reduced variability coated floss
WO2016084862A1 (fr) * 2014-11-28 2016-06-02 旭硝子株式会社 Compositions de caoutchouc fluoré et article en caoutchouc fluoré réticulé
WO2019213298A1 (fr) * 2018-05-01 2019-11-07 Texas Tech University System Fil dentaire à revêtement médicinal adaptable pour le traitement d'une maladie des gencives
US11623076B2 (en) 2018-05-01 2023-04-11 Texas Tech University System Tailorable medicinally coated floss for the treatment of gum disease

Also Published As

Publication number Publication date
GB9726909D0 (en) 1998-02-18
AU1570899A (en) 1999-07-12

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