WO1998048766A1 - Antimicrobial dental materials containing 2,4,4'-trichloro-2'-hydroxydiphenyl ether - Google Patents
Antimicrobial dental materials containing 2,4,4'-trichloro-2'-hydroxydiphenyl ether Download PDFInfo
- Publication number
- WO1998048766A1 WO1998048766A1 PCT/US1998/008465 US9808465W WO9848766A1 WO 1998048766 A1 WO1998048766 A1 WO 1998048766A1 US 9808465 W US9808465 W US 9808465W WO 9848766 A1 WO9848766 A1 WO 9848766A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dental
- triclosan
- trichloro
- antimicrobial
- hydroxydiphenyl ether
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/69—Medicaments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
- A61K6/77—Glass
Definitions
- the invention relates to polymerizable dental materials. More particularly, the invention relates to such materials having an antimicrobial effect. Specifically, the invention relates to dental materials such as protective dental varnishes, composites, compomers, fissure sealants, dental cements, dental bonding agents and similar materials, and containing 2,4, 4"-trichloro-2 '-hydroxydiphenyl ether. Background of the Invention
- PCT WO 89/10736 describes dental glasspolyalkenoate cements made soluble in oral fluids by the addition of chlorhexidine. However, these materials dissolve after 1-4 weeks on the teeth and therefore are not suitable as long-term dental materials .
- Triclosan is a highly effective antimicrobial with a broad spectrum of activity against both Gram-positive and Gram-negative bacteria as well as fungi, yeasts and viruses [Ciba-Geigy: Irgasan, Important toxicological and ecological data, 2512 E; Ciba-Geigy: Irgasan MP: General information. on chemical, physical, microbiological and toxicological properties] . In long-term experiments, no development of bacterial resistance to triclosan was found [C. L. Jones et. al., in: J. Dent. Res. 67, 46-50 (1988)].
- the above-mentioned objects can be accomplished by adding from about 0.001 to about 20 percent by weight of the broad spectrum antimicrobial agent triclosan to otherwise dental materials.
- the water solubility of triclosan is low and it is embedded in a crosslinked polymer matrix, leaching of the triclosan is low, resulting in a long-term antimicrobial effect. Incorporation of efficacious amounts of triclosan does not affect the mechanical properties of the dental materials .
- the present invention describes polymerizable dental materials that have an antimicrobial effect due to the incorporation of 2, 4, 4 ' -trichloro-2 ' - hydroxydiphenyl ether into the composition.
- Curable dental materials with an antimicrobial effect are provided for prophylactic and restorative treatment of teeth, including those materials intended for use with enamel, dentin, dental metals and the like.
- the dental materials according to the invention preferably contain a matrix of curable or hardenable resin material or materials.
- Such materials include for example, methacrylate compounds (preferably dimethacrylate) , urethane compounds and the like. Any conventional dental resin or curable dental matrix material is within the scope of the invention.
- the dental materials may also contain fillers, fluoride, stabilizers, initiators, solvents and other substances conventionally used in dental materials.
- the incorporation of triclosan into dental materials causes them to have antimicrobial properties. These antimicrobial properties lead to a reduction in caries and other dental diseases related to microorganisms. As dental materials are usually employed in situations where the tooth is either endangered or already damaged, the incorporation of triclosan into these materials has the additional advantage of getting the antimicrobial exactly to the location in the oral cavity where it is most needed or desired.
- the antimicrobial agent triclosan is embedded in a polymeric matrix. This provides the dental materials with a long-lasting antimicrobial effect as the triclosan cannot leach out of these materials quickly. This aspect of the invention will be demonstrated hereinbelow.
- the incorporation of triclosan can be employed in dental bonding agents, composite restorations, compomer restorations, fissure sealants or other conventional dental materials for which an antimicrobial effect is desirable. It has been unexpectedly found that incorporation of sufficient amounts of triclosan into these dental materials does not detrimentally affect the mechanical properties of the materials.
- These dental materials are made to have an antimicrobial effect by incorporation of from about 0.001 to about 20 percent by weight of triclosan.
- the triclosan is preferably added in the unpolymerized state of the dental materials. After curing, a polymeric network is formed that does not only harden the dental material but also serves as a matrix for the triclosan, embedding it in a way that prevents rapid leaching. This polymeric network ensures the long-term antimicrobial efficacy of the triclosan.
- An antimicrobial protective varnish for exposed dentin was prepared containing the following components .
- Example 1 Composition
- camphorquinone - 0.2 wt% camphorquinone .
- test plates were filled with 50 ⁇ l of a liquid containing approximately 5 x 10 CFU of streptococcus mutans in PBS + 10% serum. Contact time was 30 seconds, 10 minutes (min), 1 hour (h) , 3 hours and 6 hours at 37°C. An unfilled test plate was used as negative control. Each test was run three times. Subsequently the test solution was transferred to a new plate and subjected to enrichment. An MTT test was carried out to detect living streptococci mutans.
- plaques of approximately 1.2 g were made from a mixture of the varnish components of Example 1, except for the solvent ethanol (triclosan content 6.25 wt% based on resin mixture as described above) . These plaques were light-cured and stored in artificial saliva (Ringer solution) for 20 days at
- the low triclosan leaching was also proven by a different experiment. Plaques as described above were thermocycled 500 times (5°C and 55°C, 20 seconds each) . Weighing before and after thermocycling showed a weight difference of + 1% (absorption of some water) and not the loss of 6.25% to be expected if all the triclosan had leached out.
- plaques of approximately 1.2 g (width 2 mm, diameter 25 mm) with varying triclosan contents (wt% based on resin mixture) were made from a mixture of the varnish components of Example 1, except for the solvent ethanol. Different mixture ratios of the resins were used. The plaques were light-cured, and Barcol hardness was measured.
- the hardness of the antimicrobial varnish containing low triclosan concentrations was found to be as high as the hardness of the varnish not containing any triclosan. Only at higher triclosan concentrations the hardness of the varnish dropped.
- Thermocycling (500 cycles, 20 seconds at 5°C, 20 seconds at 55°C) does lower hardness somewhat, but not significantly more than with the formulation not containing any triclosan. Mechanical test results are reported in Table IV.
- a composite restorative material was mixed from 73.7% glass filler (Barium Aluminum Corning 7724 glass
- EBPADMA urethane resin ethoxylated bisphenol-A-dimethacrylate urethane resin
- Test plates were each filled with a single cylindric sample (diameter 5 mm, height approximately 2 mm) of cured composite material. These test plates were filled with 50 ⁇ l of a liquid containing approximately 5 x 10 CFU of streptococcus mutans in PBS + 10% serum. Contact time was 30 seconds, 10 min, 1 hour, 3 hours and 6 hours at 37 °C. An unfilled test plate was used as negative control. Each test was run three times. Subsequently the test solution was transferred to a new plate and subjected to enrichment. An MTT test was carried out to detect living streptococci mutans.
- the bonding agent was composed of the following materials.
- camphorquinone - 0.2 wt% camphorquinone .
- test plates were filled with 50 ⁇ l of a liquid containing approximately 5 x 10 CFU of streptococcus mutans in PBS + 10% serum. Contact time was 30 seconds, 10 min, 1 hour, 3 hours and 6 hours at 37°C. An unfilled test plate was used as negative control. Each test was run three times. Subsequently the test solution was transferred to a new plate and subjected to enrichment. An MTT test was carried out to detect living streptococci mutans.
- Table VII antimicrobial effect of triclosan- containing dental bonding agent at first and second elution
- Bond strength was determined by the shear bond strength of the composite resin in relation to enamel and dentin. Human molars were used. For purposes of enamel bond tests, the enamel surface of 6 human molars was polished with carborund (SiC) . This fresh, dry enamel surface was treated with the etching solution for 20 seconds, followed by compressed air drying. Thereafter, the bonding agent was applied and, 20 seconds later, compressed air drying was effected. This coat was light-cured for 20 seconds, using a Spectrum curing light (Dentsply International Inc.). Subsequently, a plastic mold with an inner diameter of 5 mm and a height of 2 mm was fixed to the surface and TPH Spectrum was filled into the interior of the mold.
- CeC carborund
- the surface was subjected to visible light irradiation by the Spectrum curing light via the mold for 40 seconds. After light-curing, the teeth were stored at 37 °C for 24 hours, then thermocycled 500 times (20 seconds at 5°C, 20 seconds at 55°C) , embedded in gypsum and tested with a Zwick Z010/TN2A tabletop universal testing machine at a speed of 1 millimeter per minute (mm/ min) .
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- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Dental Preparations (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU72604/98A AU7260498A (en) | 1997-04-28 | 1998-04-27 | Antimicrobial dental materials containing 2,4,4'-trichloro-2'-hydroxydiphenyl ether |
JP54725598A JP2001524113A (en) | 1997-04-28 | 1998-04-27 | Dental antibacterial material containing 2,4,4'-trichloro-2'-hydroxydiphenyl ether |
EP98919924A EP0980234A1 (en) | 1997-04-28 | 1998-04-27 | Antimicrobial dental materials containing 2,4,4'-trichloro-2'-hydroxydiphenyl ether |
CA002288331A CA2288331A1 (en) | 1997-04-28 | 1998-04-27 | Antimicrobial dental materials containing 2,4,4'-trichloro-2'-hydroxydiphenyl ether |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US4499597P | 1997-04-28 | 1997-04-28 | |
US96079097A | 1997-10-30 | 1997-10-30 | |
US60/044,995 | 1997-10-30 | ||
US08/960,790 | 1997-10-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998048766A1 true WO1998048766A1 (en) | 1998-11-05 |
Family
ID=26722256
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1998/008465 WO1998048766A1 (en) | 1997-04-28 | 1998-04-27 | Antimicrobial dental materials containing 2,4,4'-trichloro-2'-hydroxydiphenyl ether |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0980234A1 (en) |
JP (1) | JP2001524113A (en) |
AU (1) | AU7260498A (en) |
CA (1) | CA2288331A1 (en) |
WO (1) | WO1998048766A1 (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999042080A2 (en) * | 1998-02-19 | 1999-08-26 | Oraceutical, Llc | Curable compositions with antimicrobial properties |
WO2001095862A1 (en) * | 2000-06-13 | 2001-12-20 | Dentsply International Inc. | Low shrinking polymerizable dental material |
WO2002062303A1 (en) * | 2001-02-07 | 2002-08-15 | Despina Kostomiri | Method of tooth whitening with synthetic resin in white liquid nail-polish type |
US7495037B2 (en) | 2003-08-29 | 2009-02-24 | Ivoclar Vivadent Ag | Dental coating materials |
US7553881B2 (en) | 2006-04-28 | 2009-06-30 | Ivoclar Vivadent Ag | Dental materials based on radically polymerizable macromers with antimicrobial effect |
US8222315B2 (en) | 2005-11-11 | 2012-07-17 | Ivoclar Vivadent Ag | Method for producing composites that can be used in dentistry |
EP2489344A1 (en) | 2011-02-15 | 2012-08-22 | Ivoclar Vivadent AG | Dental material based on an anti-microbial compound |
US8933147B2 (en) | 2005-11-17 | 2015-01-13 | 3M Innovative Properties Company | Anti-microbial dental impression material |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8329674B2 (en) * | 2007-07-25 | 2012-12-11 | 3M Innovative Properties Company | Film forming dental compositions and related methods |
JP5435892B2 (en) | 2008-05-21 | 2014-03-05 | 株式会社トクヤマデンタル | Photopolymerizable composition |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1989010113A1 (en) * | 1988-04-26 | 1989-11-02 | Rijksuniversiteit Te Groningen | Antimicrobial composition with long-term activity |
WO1992004890A1 (en) * | 1990-09-20 | 1992-04-02 | The Procter & Gamble Company | Sustained release compositions for treating periodontal disease |
-
1998
- 1998-04-27 EP EP98919924A patent/EP0980234A1/en not_active Withdrawn
- 1998-04-27 CA CA002288331A patent/CA2288331A1/en not_active Abandoned
- 1998-04-27 WO PCT/US1998/008465 patent/WO1998048766A1/en not_active Application Discontinuation
- 1998-04-27 AU AU72604/98A patent/AU7260498A/en not_active Abandoned
- 1998-04-27 JP JP54725598A patent/JP2001524113A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1989010113A1 (en) * | 1988-04-26 | 1989-11-02 | Rijksuniversiteit Te Groningen | Antimicrobial composition with long-term activity |
WO1992004890A1 (en) * | 1990-09-20 | 1992-04-02 | The Procter & Gamble Company | Sustained release compositions for treating periodontal disease |
Non-Patent Citations (2)
Title |
---|
IMAZATO S ET AL: "Antibacterial effect of composite incorporating Triclosan against Streptococcus mutans.", JOURNAL OF THE OSAKA UNIVERSITY DENTAL SCHOOL, (1995 DEC) 35 5-11. JOURNAL CODE: JIV. ISSN: 0473-4599., Japan, XP002074014 * |
IMAZATO S ET AL: "Incorporation of bacterial inhibitor into resin composite.", JOURNAL OF DENTAL RESEARCH, (1994 AUG) 73 (8) 1437-43. JOURNAL CODE: HYV. ISSN: 0022-0345., United States, XP002074015 * |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999042080A2 (en) * | 1998-02-19 | 1999-08-26 | Oraceutical, Llc | Curable compositions with antimicrobial properties |
WO1999042080A3 (en) * | 1998-02-19 | 1999-10-07 | Oraceutical Llc | Curable compositions with antimicrobial properties |
US6281265B1 (en) | 1998-02-19 | 2001-08-28 | Salim A. Nathoo | Curable compositions with antimicrobial properties |
WO2001095862A1 (en) * | 2000-06-13 | 2001-12-20 | Dentsply International Inc. | Low shrinking polymerizable dental material |
WO2002062303A1 (en) * | 2001-02-07 | 2002-08-15 | Despina Kostomiri | Method of tooth whitening with synthetic resin in white liquid nail-polish type |
KR100853735B1 (en) * | 2001-02-07 | 2008-08-25 | 데스피나 코스토미리 | Method of Tooth Whitening with White Liquid Synthetic Resin |
US7495037B2 (en) | 2003-08-29 | 2009-02-24 | Ivoclar Vivadent Ag | Dental coating materials |
US8222315B2 (en) | 2005-11-11 | 2012-07-17 | Ivoclar Vivadent Ag | Method for producing composites that can be used in dentistry |
US8933147B2 (en) | 2005-11-17 | 2015-01-13 | 3M Innovative Properties Company | Anti-microbial dental impression material |
US7553881B2 (en) | 2006-04-28 | 2009-06-30 | Ivoclar Vivadent Ag | Dental materials based on radically polymerizable macromers with antimicrobial effect |
EP2489344A1 (en) | 2011-02-15 | 2012-08-22 | Ivoclar Vivadent AG | Dental material based on an anti-microbial compound |
Also Published As
Publication number | Publication date |
---|---|
AU7260498A (en) | 1998-11-24 |
CA2288331A1 (en) | 1998-11-05 |
EP0980234A1 (en) | 2000-02-23 |
JP2001524113A (en) | 2001-11-27 |
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