AU602012B2 - Dental material for the control of caries and paradentitis - Google Patents
Dental material for the control of caries and paradentitis Download PDFInfo
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- AU602012B2 AU602012B2 AU79557/87A AU7955787A AU602012B2 AU 602012 B2 AU602012 B2 AU 602012B2 AU 79557/87 A AU79557/87 A AU 79557/87A AU 7955787 A AU7955787 A AU 7955787A AU 602012 B2 AU602012 B2 AU 602012B2
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- Australia
- Prior art keywords
- dental material
- dental
- chlorhexidine
- material according
- caries
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- 239000005548 dental material Substances 0.000 title claims description 27
- 208000002925 dental caries Diseases 0.000 title claims description 15
- 239000013543 active substance Substances 0.000 claims abstract description 32
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 claims abstract description 26
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229960003260 chlorhexidine Drugs 0.000 claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 15
- 239000005844 Thymol Substances 0.000 claims abstract description 13
- 229960000790 thymol Drugs 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- HHTWOMMSBMNRKP-UHFFFAOYSA-N carvacrol Natural products CC(=C)C1=CC=C(C)C(O)=C1 HHTWOMMSBMNRKP-UHFFFAOYSA-N 0.000 claims abstract description 8
- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 235000007746 carvacrol Nutrition 0.000 claims abstract description 8
- WYXXLXHHWYNKJF-UHFFFAOYSA-N isocarvacrol Natural products CC(C)C1=CC=C(O)C(C)=C1 WYXXLXHHWYNKJF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002966 varnish Substances 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- -1 fluoride ions Chemical class 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 235000010585 Ammi visnaga Nutrition 0.000 claims description 3
- 244000153158 Ammi visnaga Species 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 229940072049 amyl acetate Drugs 0.000 claims description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 241000371652 Curvularia clavata Species 0.000 claims 1
- 239000003479 dental cement Substances 0.000 claims 1
- 210000000214 mouth Anatomy 0.000 abstract description 5
- 239000004568 cement Substances 0.000 abstract description 3
- 239000004922 lacquer Substances 0.000 abstract 1
- 210000004268 dentin Anatomy 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 230000000845 anti-microbial effect Effects 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000000069 prophylactic effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 239000003722 gum benzoin Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Chemical compound CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- WJLVQTJZDCGNJN-UHFFFAOYSA-N Chlorhexidine hydrochloride Chemical compound Cl.Cl.C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 WJLVQTJZDCGNJN-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 238000002768 Kirby-Bauer method Methods 0.000 description 1
- 206010039424 Salivary hypersecretion Diseases 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000194019 Streptococcus mutans Species 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- SHOKWSLXDAIZPP-UHFFFAOYSA-N [4-(4-iodooxy-2-methyl-5-propan-2-ylphenyl)-5-methyl-2-propan-2-ylphenyl] hypoiodite Chemical compound C1=C(OI)C(C(C)C)=CC(C=2C(=CC(OI)=C(C(C)C)C=2)C)=C1C SHOKWSLXDAIZPP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- LFVVNPBBFUSSHL-UHFFFAOYSA-N alexidine Chemical compound CCCCC(CC)CNC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NCC(CC)CCCC LFVVNPBBFUSSHL-UHFFFAOYSA-N 0.000 description 1
- 229950010221 alexidine Drugs 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- WDRFFJWBUDTUCA-UHFFFAOYSA-N chlorhexidine acetate Chemical compound CC(O)=O.CC(O)=O.C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 WDRFFJWBUDTUCA-UHFFFAOYSA-N 0.000 description 1
- 229960001884 chlorhexidine diacetate Drugs 0.000 description 1
- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007542 hardness measurement Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 210000004261 periodontium Anatomy 0.000 description 1
- 229960005100 picloxydine Drugs 0.000 description 1
- YNCLPFSAZFGQCD-UHFFFAOYSA-N picloxydine Chemical compound C=1C=C(Cl)C=CC=1N=C(N)N=C(N)N(CC1)CCN1C(N)=NC(N)=NC1=CC=C(Cl)C=C1 YNCLPFSAZFGQCD-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001432 tin ion Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/20—Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Dental Preparations (AREA)
- Dental Tools And Instruments Or Auxiliary Dental Instruments (AREA)
Abstract
The material contains a combination of the active substances thymol and/or carvacrol and chlorhexidine and/or the physiologically tolerated salts thereof. The material can be a dental lacquer or cement or the like which remains for a lengthy period in the oral cavity and out of which the combination of active substances can diffuse.
Description
LI COMMONWEALTH OF AUSTRALIA Patents Act i6 0 2 0 COMPLETE SP E.C I F.I-CI.A T I ON
(ORIGINAL)
Application Number Lodged This document contains the amendments made under Section 49 and is correct for printing.
Complete Specification Lodged Accepted Published Priority 11 October 1986
I
Related Art Name of Applicant Address of Applicant Actual Inventor/s Address for Service IVOCLAR AG P.O. Box FL-9494, Schaan, Liechtenstein Rudolf J. Michl RICE CO., Patent Attorneys, 28A Montague Street, Balmain N.S.W. 2041 Complete Specification for the invention entitled: DENTAL MATERIAL FOR THE CONTROL OF CARIES AND PARADENTITIS The following statement is a full description of this invention including the best method of performing it known to us:i. ila- The invention relates to the subject matter of claims 1 to Despite research over many decades and numerous attempts to achieve prophylactic and therapeutic treatment of caries and paradentitis, they still constitute an unmastered problem.
°o Medical treatment has hitherto largely been based on fluorides, a cf. Dr. Hans Joachim Schmidt, "Zahnhalskariesprophylaxe durch oo Fluoride", Dr. Alfred Huthig Verlag, Heidelberg, 2nd edition, 1967.
CO
0 However, it is only appropriate to administer fluoride tablets up to o 0 the end of tooth formation, i.e. up to about 12 years of age. After this time, it is mainly a question of the local application of active 0 0 substances for the prophylactic and therapeutic treatment of caries 0 4 S and paradentitis.
o° Fluorides and other active substances and in particular anti- B° microbially active substances have hitherto been largely incorporated oO into mouth and tooth treatment products and have been used during daily oral hygiene. However, the action period thereof is short, because the active substances are very rapidly diluted and rinsed out as a result of permanent salivation and the absorption of food.
To obviate these disadvantages, it has already been proposed for therapeutic treatment of paradentitis to introduce into the parodontium antimicrobially active substances such as chlorhexidine embedded in a film as a system with delayed active substance delivery, i: i? 2 cf. Coventry, J. and Newman, J. Clin. Periodontol. 9, 129-133 (1982) and Friedman, M. and Golomb, J. Periodontol. 17, 323-328 (1982). A further chlorhexidine-containing system with delayed active substance delivery for use in the dental area was described by T.E.Balanyk and H.J.Sandham in J. Dent.Res. 64, 1356-1360 (1985). It consists of a solution of a chlorhexidine salt in benzoin resin, which forms a firm film on drying from which the active substance is delivered in a delayed manner. The described in vitro tests reveal that i0 after 14 days only 3 to 10 mg of chlorhexidine had been supplied by the system and the remaining active substance was not available. Table 1 also shows that the antiseptics thymol s and iodine are the least effective.
The problem of the present invention is to provide an agent S for the effective prophylactic and therapeutic control of caries and paradentites and in particular dental neck caries, Swhich remains over a long period or permanently in the oral cavity, so that it has a longer action period as a treatment L'-0 agent for the mouth and teeth and whilst avoiding the Saforementioned disadvantages has an improved antimicrobial Sactivity, whilst also hardening the attacked dentine.
O 0 Goe This problem is solved according to the invention.
e It has surprisingly been found that the inventive use of a 4 combination of the antimicrobial active agents thymol and/or o carvacrol of formulas CH3 CH,
OH
OH O H
CH
3 C H CH 3 Jlp- -3o o o
OC
0 0 0 a 0 and the antimicrobial active agent chlorhexidine of formula NH H NH NH c1-a NH-C-NH-C-H-ICH-NH-C-NH-NH -0 -a and/or physiologically compatible salts thereof in a dental material, results in an increase in themicrobicidal activity of these substances. In addition surprisingly there is a significant and selective hardening of the carious dentine through the use of the S active substance combination of thymol and/or carvacrol and 0 chlorhexidine or salts thereof in a dental material.
o The active agent combination can be used in any dental material as a carrier, which can be hardened or is hard and i Q from which the active substances can diffuse. Preferably use is made of a material from which the active substances can diffuse into the dentine.
According to the invention the term "dental material"leevers those carrier materials, which remain for a certain period, from hours to years in the oral cavity.
According to a preferred embodiment of the invention the carrier is constituted by a solution of colophony in an organic solvent, particularly preferred solvents being ethanol, propanol and amyl acetate. Good results have also been obtained with e.g. 1,2- )0 dichloroethylene. The solution can be applied to the dental neck by painting, dripping or spraying and form there a firmly adhering varnish, which serves as the active agent reservoir and from which the active agent combination uniformly and completely diffuses ^w^i~ ,j .s 0~d0 L -1" 4 into the dentine.
It has also proved effective to apply the dental material, e.g. as a dental varnish to a solid substrate, where it optionally may harden. According to the invention the term "solid substrate" indicates substrates like artificial teeth, crowns and bridges, toothpicks, toothsilk and similar devices, to which the dental material of the invention can be applied and subsequent to the use or mounting of which within the 1 Q mouthcavity the combination of the invention can develop its activity.
For example a toothvarnish may be applied to the tip of a toothpick and the active agent combination of the invention may be applied to the teeth when cleaning the same.
According to further embodiments of the invention the active agent combination is incorporated into dental materials such as cements, underfilling, filling, sealing, fixing, prosthetic, crown cLO and bridge materials, as well as materials for producing prostheses or in adhesives.
Thymol and/or carvacrol is used in a quantity of approximately to 0.05% by weight, preferably 5 to 0.25% by weight and in particularly preferred manner 2 to 0.5% by weight, in each case based on the dental material. Chlorhexidine is used in a quantity of approximately 2 to 0.01% by weight, preferably I to 0.05% by weight and in particularly preferred manner 0.5 to 0.1% by weight, also based on the dental material.
The aforementioned active substances can be used as such, or in JO3 the form of their physiologically compatible salts.
5 o o c o 4i Usable chlorhexidine salts are e.g. chlorhexidine-di-D-gluconate, chlorhexidine-dihydrochloride and chlorhexidine-diacetate. According to the invention, it is also possible to use related compounds of chlorhexidine such as alexidine, picloxydine or vantocil, as well as those of thymol,such as e.g. aristol.
The inventive dental material can also contain fluoride ions, e.g. in the form of sodium fluoride, in quantities of e.g. 5 to 0.05 and preferably 2 to 0.1% by weight, based on the total formulation.
In place of fluoride ions, it is also possible to use zinc ions, e.g.
as chloride or acetate, tin ions, e.g. as chloride, divalent copper ions, e.g. as copper nitrate and molybdenum ions, e.g. as Na 2 Mo0 4 ,2H 2 0 or mixtures thereof.
The inventive dental material acts both prophylactically and therapeutically against bacteria, the action time being essentially dependent on the carrier system chosen. If, e.g. accrrding to a preferred embodiment of the invention, a solution of colophony is used in high percent ethanol, then it can be painted, dripped or sprayed as a varnish, particularly on to the dental neck. This varnish adheres for a certain time and during this period delivers the active substances contained in an almost complete form to the dental neck.
Although the varnish is removed after a relatively short time by saliva, it maintains its therapeutic action over a longer period. Surprisingly there is a rapid diffusion of the inventive active substance combination into the dentine and from there a uniform delivery of active agent is taking place. This was not foreseeable. The susceptibility of the dental neck to bacteria is consequently considerably reduced and, to the extent that an attack has already taken place, the dentine is hardened and stabilized against spread of the attack.
4 4 44*r ii 6 oio Go 0 00a 33 0 3 030R 33 Carrier materials for dental, varnishes are alsc shellac, benzoin resin, polyvinylpyrrolidone or other artificial or natural resins, which can be dissolved in a solvent and which after evaporation of the solvent become hard.
If the inventive active agent combination is incorporated into cements or other dental materials, then a uniform active agent delivery can take place over a period of several weeks and months.
For example the inventive active agent combination can be incorporated into an underfilling material and then the constant delivery of the active agents effectively prevents the occurrence of secondary caries.
It is also conceivable to incorporate the antibacterial substance combination into a light-hardening or conventionally curing filling material, in order to decrease the rate of formation of secondary caries. Further the active agents used according to the invention can also be incorporated into prosthetic materials, so that the finished prosthesis constantly delivers very small amounts of the active substances and consequently counteracts the spread of plaque, which would lead to caries on the natural teeth which are still present. The invention has a similar effect in false teeth.
Underfilling materials, filling materials, prosthetic materials, false teeth, etc. are well known to the Expert and do not form part of the invention. Such dental materials are e.g. disclosed in DE-OS 24 03 211, DE-OS 27 49 564 and US patent 3 047 408.
The invention is further illustrated hereinafter by means of examples.
A -7- EXAMPLE 1 Preparation of a Varnish 3 g of colophony are placed in a flask, mixed with 6 ml of pure 96% ethanol and after sealing the flask undergoes shaking for 24 hours until they dissolve. 2 ml of distilled water are added to the solution, followed oy 0.1 g of thymol, 0.02 g of chlorhexidine and 0.01 g of sodium fluoride,. being dissolved by shaking again in the liquid. The varnish obtained is stored in a sealed plastic vessel at room temperature.
,I
'Ic: 8 EXAMPLE 2 The activity of the varnish according to example 1 on the dentine of healthy and carious cattle teeth was investigated in the following way.
Cattle teeth were kept initially for 14 days at 37°C in an artificial caries solution. The solution contained 6% by weight of carboxymethyl cellulose and the pH-value was 4.5. The teeth were completely covered with solution throughout this period. The teeth were then removed, rinsed with water and dried.
In two successive tests, in each case 5 of the teeth treated with S 0 the caries solution and 5 untreated, healthy cattle teeth were coated 0 0 o S with the varnish prepared according to example 1. The action of the varnish on the dentine hardness was determined, in that the Knoop hardness (500 g load) of the varnish-coated teeth was determined in comparison with the corresponding teeth not coated with the varnish.
The results are given in table 1.
oi V Table 1 Knoop hardness measurement length of the impression in pm Dentine Without Caries Dentine With Caries oL Test Without Varnish With Varnish Without Varnish With Varnish 1 358 25 350 18 1233 t 96 970 71 2 356 24 343 29 1200 75 1063 t 61 The results show that the hardness of the healthy, untreated dentine is not or is only insignificantly influenced by the inventive varnish according to example 1. However, the hardness of the carious dentine is significantly improved by the varnish treatment.
_i I 9 EXAMPLE 3 The antimicrobial activity of the inventive active substance combination was proved in the agar diffusion test using streptococcus mutans.
The following test solutions were used: A) Varnish according to example 1 B) Varnish according to example 1 without fluoride ions C) Varnish according to example I without thymol S, D) Varnish according to example 1 without chlorhexidine.
o a 0 0.05 ml of each solution was brought on to the streptococcus es mutans-inoculated agar plates on a Petri dish and the diameters of the inhibition zones after incubating the plates for 18 hours were measured at 37°C. The results are given below in table 2.
Table 2 Test Solution Inhibition Zone Diameter, mm A B SC SD 13 A )0 The results given in table 2 show that the antimicrobial effect of the combination of thymol and chlorhexidine is considerably improved compared with that of the individual components alone. However, the presence of fluoride ions did not influence the inhibition zone diameter.
-jci
Claims (8)
1. Dental material as hereinbefore defined for the control of caries and paradentitis with a content of antibacterial active substances, characterized in that it contains a combination of thymol and/or carvacrol with chlorhexidine in a dental material as the carrier. 2, Dental material according to claim 1 wherein at least part of the chlorhexidine is a physiologically compatible salt thereof.
3. Dental material according to claim 1, characterized in that it contains the thymol and/or carvacrol or salts 0 00 ao thereof in a quantity of 10 to 0.05% by weight and the Sn a chlorhexidine or salts thereof in a quantity of 2 to 0.01% 0 o° by weight, in each case based on the dcntal material. 000 Q0 oooQO 4. Dental material according to either one of claims 1 or 2, characterized in that it contains the thymol and/or carvacrol or the salts thereof in a quantity of 5 to 0.25, preferably 2 to 0.5% by weight and the chlorhexidine or the salts thereof in a quantity of 1 to 0.05, preferably to 0.1% by weight. Dental material according to any one of the claims 1 to 4, characterized in that it additionally contains fluoride ions.
6. Dental material according to any one of the claims 1 to 5, characterized in that the material is a dental varnish, dental cement, underfilling, prosthetic, crown, bridge, filling, sealing or fastening material or adhesive.
7. Dental material according to claim 6, characterized in that the material is a dental varnish based on a solution of colophony in an organic solvent.
8. Dental material according to claim 7, characterized in that the organic solvent is ethanol, propanol or amyl acetate. 'q 06. L N 11
9. A dental material, as hereinbefore defined, comprising a combination of thymol and/or carvacrol with chlorhexidine or physiologically compatible salts thereof, when used for the control of caries and paradentitis A method of controlling caries and/or paradentitis wherein the dental material according to any one of claims 1-8 is applied to a solid substrate and is introduced into the mouthcavity by means of said solid substrate.
11. The method according to claim 10, characterized in that the solid substrate is a toothpick.
12. A dental material substantially as described with S. reference to Examples 1 and 2. 0 o DATED this 14 day of May 1990 o o IVOCLAR AG o Patent Attorneys for the F.B. RICE CO; k 5
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863634697 DE3634697A1 (en) | 1986-10-11 | 1986-10-11 | DENTAL MATERIAL TO CONTROL CARIES AND PERIODONTOSE |
| DE3634697 | 1986-10-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7955787A AU7955787A (en) | 1988-04-14 |
| AU602012B2 true AU602012B2 (en) | 1990-09-27 |
Family
ID=6311547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU79557/87A Ceased AU602012B2 (en) | 1986-10-11 | 1987-10-12 | Dental material for the control of caries and paradentitis |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0264660B1 (en) |
| AT (1) | ATE77229T1 (en) |
| AU (1) | AU602012B2 (en) |
| CA (1) | CA1332812C (en) |
| DE (2) | DE3634697A1 (en) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5156835A (en) * | 1987-01-30 | 1992-10-20 | Colgate-Palmolive Company | Antibacterial antiplaque oral composition |
| US5192530A (en) * | 1987-01-30 | 1993-03-09 | Colgate-Palmolive Company | Antibacterial antiplaque oral composition |
| US5180578A (en) * | 1987-01-30 | 1993-01-19 | Colgate-Palmolive Company | Antibacterial antiplaque anticalculus oral composition |
| US5188821A (en) * | 1987-01-30 | 1993-02-23 | Colgate-Palmolive Company | Antibacterial antiplaque oral composition mouthwash or liquid dentifrice |
| US5178851A (en) * | 1987-01-30 | 1993-01-12 | Colgate-Palmolive Company | Antiplaque antibacterial oral composition |
| US5192531A (en) * | 1988-12-29 | 1993-03-09 | Colgate-Palmolive Company | Antibacterial antiplaque oral composition |
| US5160737A (en) * | 1988-05-03 | 1992-11-03 | Perio Products Ltd. | Liquid polymer composition, and method of use |
| GB8810412D0 (en) * | 1988-05-03 | 1988-06-08 | Ici Plc | Hard tissue surface treatment |
| US5330746A (en) * | 1988-05-03 | 1994-07-19 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Dental varnish composition, and method of use |
| US5438076A (en) * | 1988-05-03 | 1995-08-01 | Perio Products, Ltd. | Liquid polymer composition, and method of use |
| SE8801719D0 (en) * | 1988-05-06 | 1988-05-06 | Dan W Ericson | ANTIBACTERIAL DENTIFICATION AND CEMENTATION MATERIAL |
| US4992276A (en) * | 1988-12-14 | 1991-02-12 | Warner-Lambert Company | Antiseptic compositions containing hexahydro-5-pyrimidinamine compounds and thymol and methods for preparing same |
| US5139768A (en) * | 1989-01-31 | 1992-08-18 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Dental composition for hypersensitive teeth |
| US5116603A (en) * | 1989-01-31 | 1992-05-26 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Oral antifungal preventative, and method of use |
| DE4019617A1 (en) * | 1990-06-20 | 1992-01-02 | Thera Ges Fuer Patente | IMPLANTABLE ACTIVE SUBSTITUTE MATERIAL |
| IT1272191B (en) * | 1994-03-28 | 1997-06-16 | Bandini Srl | COMPOSITION OF SYNTHETIC RESIN-BASED DENTAL MATERIAL WITH ANTISEPTIC PROPERTIES. |
| HUP9802533A3 (en) * | 1995-10-11 | 1999-08-30 | Warner Lambert Co | Antimicrobial oral compositions containing a c3-c6 alcohol |
| US5891422A (en) * | 1996-10-10 | 1999-04-06 | Warner-Lambert Company | Antimicrobial composition containing a C3 -C6 alcohol |
| CA2309980A1 (en) * | 1997-11-13 | 1999-05-27 | Espe Dental Ag | Metal-free dental filling system as a substitute for amalgam |
| US6407148B1 (en) | 1997-11-13 | 2002-06-18 | 3M Espe Ag | Metal-free dental filling system as a substitute for amalgam |
| EP1000616A1 (en) * | 1998-09-25 | 2000-05-17 | Mathias Jozef Maria Schaeken | Prevention and treatment of parodontitis |
| EP1137426B1 (en) | 1998-12-07 | 2005-10-26 | Ecosmart Technologies, Inc. | Breast cancer treatment using natural plant essential oils |
| DE10339912B4 (en) | 2003-08-29 | 2016-07-21 | Ivoclar Vivadent Ag | Dental coating materials, their use and methods of coating a substrate surface |
| US7335691B2 (en) | 2004-07-02 | 2008-02-26 | Scientific Pharmaceuticals, Inc. | Caries preventive desensitizing and fluoridizing dental varnishes |
| EP1778361A4 (en) * | 2004-07-29 | 2012-04-04 | Reeve Tammy Rene | ANTIMICROBIAL AND / OR ANTIVIRAL COMPOSITION AND METHODS OF PREPARATION AND ADMINISTRATION THEREOF |
| WO2006120495A1 (en) * | 2005-05-13 | 2006-11-16 | Advanced Scientific Developements | Pharmaceutical composition comprising an antiviral agent, an antitumour agent or an antiparasitic agent and an active substance selected from carveol, thymol, eugenol, borneol and carvacrol |
| WO2006120494A1 (en) * | 2005-05-13 | 2006-11-16 | Advanced Scientific Developements | Pharmaceutical combination comprising an antibacterial agent and an active substance selected from carveol, thymol, eugenol, borneol and carvacrol |
| DE102008051543A1 (en) | 2008-10-14 | 2010-04-15 | Epg (Engineered Nanoproducts Germany) Ag | Long-term stable, microbicidal and biofilm formation preventing coating and coating composition therefor |
| CA2901431C (en) | 2013-02-15 | 2017-10-17 | Dentsply International Inc. | Dental varnish compositions comprising rosin, resin, and a fluoridizing agent |
| IT201900018752A1 (en) | 2019-10-14 | 2021-04-14 | Alessandro Tosetti | COMPOSITION BASED ON ESSENTIAL OILS FOR DENTAL USE FOR THE TREATMENT OF PERIODONTITIS AND PERIMPLANT MUCOSITE |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3390456A (en) * | 1964-01-02 | 1968-07-02 | Joseph A. Deleva | Dental composition and method of use |
| EP0055023A3 (en) * | 1980-12-18 | 1982-12-15 | E.R. Squibb & Sons, Inc. | Antiseptic containing adhesive composition |
| US4496322A (en) * | 1983-05-11 | 1985-01-29 | University Of Toronto Innovations Foundation | Benzoin antimicrobial dental varnishes |
| EP0223245A3 (en) * | 1985-11-21 | 1989-05-10 | Mitsui Petrochemical Industries, Ltd. | Curable compositions for dental drugs having sustained release property |
-
1986
- 1986-10-11 DE DE19863634697 patent/DE3634697A1/en not_active Ceased
-
1987
- 1987-09-26 AT AT87114086T patent/ATE77229T1/en not_active IP Right Cessation
- 1987-09-26 EP EP87114086A patent/EP0264660B1/en not_active Expired - Lifetime
- 1987-09-26 DE DE8787114086T patent/DE3779855D1/en not_active Expired - Lifetime
- 1987-09-28 CA CA000548019A patent/CA1332812C/en not_active Expired - Fee Related
- 1987-10-12 AU AU79557/87A patent/AU602012B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP0264660B1 (en) | 1992-06-17 |
| DE3779855D1 (en) | 1992-07-23 |
| DE3779855T (en) | 1992-07-23 |
| CA1332812C (en) | 1994-11-01 |
| EP0264660A3 (en) | 1989-04-05 |
| DE3634697A1 (en) | 1988-04-21 |
| ATE77229T1 (en) | 1992-07-15 |
| AU7955787A (en) | 1988-04-14 |
| EP0264660A2 (en) | 1988-04-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |