MXPA97005403A

MXPA97005403A - Methods, compositions and distribuciondental systems for the protection of dien surfaces

Info

Publication number: MXPA97005403A
Application number: MXPA/A/1997/005403A
Authority: MX
Inventors: K Dunton Ronald; M Homola Andrew
Original assignee: K Dunton Ronald; M Homola Andrew
Priority date: 1995-01-17
Filing date: 1997-07-16
Publication date: 1998-02-01

Abstract

The present invention describes applicators containing cationic active surface agents, hydrophobic barrier forming materials and antimicrobial compounds which, upon application to dental surfaces, form a protective film and which inhibits bacterial

Description

METHODS COMPOSITIONS AND DENTAL DISTRIBUTION SYSTEMS FOR THE PROTECTION OF THE SURFACES OF THE TEETH DESCRIPTION OF THE INVENTION The present invention relates to oral hygiene and specifically to methods of treating the oral cavity with a dental distribution system, such as a dental floss or toothpick, with cleaning, conditioning and antimicrobial properties; which are provided to the teeth with an impenetrable barrier of protection. The present invention also relates to compositions and dental delivery systems that have improved cleaning, conditioning, and antimicrobial properties, which provide the teeth with an impenetrable barrier of protection. The present invention also relates to novel cationic surfactants especially suitable for use in the present compositions, methods, and dental delivery systems. The oral care industry and health research communities have for many years sought a way to prohibit the attack, spread, growth or colonization of bacteria on teeth since attached bacteria are the beginning of a pernicious chain of events leading to the formation of plaque resistant homes, calculations, and finally, tooth loss. As people in developed countries live longer, dental care plays a very important role in overall health, and developing countries have come to take into account the importance of oral hygiene. The dental plaques that result when the calogenic bacteria (for example, Streptococcus mutans) join in colonies and form deposits on tooth surfaces. The presence of bacteria and deposits is extremely detrimental to the health of the tooth so, if it is not checked, it can result in infected gingival tissue, the formation of dental caries and possible periodontal diseases. In extreme cases its presence can still result in the loss of teeth. Many attempts have been made to control or prevent both the presence of dental caries and the formation of dental plaque. For example, fluoride solutions or gels have been used. Treatment with these materials is typically performed in a dental office periodically, but not at frequent intervals. Such treatments are primarily intended to improve the enamel of the tooth to make it more resistant to the acid action caused by the plaque. Not doing this, however, results in a plaque control for an extended period as the plaque re-establishes itself on the tooth rapidly after ingestion of food. Even when the frequency of application of such solutions and gels increases, only the partial control has been shown. For example, studies in which a solution containing fluoride (a fluoride concentration of 1%) has been applied 4 to 5 times over the course of a year demonstrate that this technique has only limited success due to the rapid re-establishment of the plaque in the oral cavity. Moreover, the daily application of a fluoride gel by means of a mounting polyvinyl tooth for sale for a period of twenty-one months, also does not show a substantial change in plaque formation between treated and untreated patients (see "Clinical Anticaries Effect of A Repeated Sodium Fluoride Application by Mouthpiece," Journal of the American Dental Association, vol 75, No. 3, September, 1967, pages 638-644. Proper use of dental floss is necessary to clean the area Considerable amount of interproximal tooth surfaces, which can not be reached by the bristles of a toothbrush The purpose of using dental floss is: 1. To dislodge and remove any decomposing food material that has accumulated on the surfaces. interproximal that can not be removed by brushing; and 2. dislodge and remove as much as possible the growth of bacterial material (plaque) on the teeth or the superimposed calculations that have been accumulated since the previous cleaning. The concept of using dental floss to clean interproximal spaces seems to have been introduced by Parmly in 1819 ("Practical Guide to the Management of the Theeth," Collins &Croft, Philadelphia, PA). Parmly has suggested the use of waxed silk to clean the teeth of people subject to gingival inflammation. Numerous types of silks have been developed and used for cleaning, until finally in 1948 Bass establishes the optimal characteristics of dental floss (Dental items of Interest, vol.70, pp. 921-34, (1948)). Most of the silks sold at least currently are also "waxed" to help penetration to the interproximal regions; as the "rope" effect described by Bass makes the wax packing difficult to force between the close spaces of the teeth. From 1960 to 1962, numerous clinical studies reported that there is no clinical difference between plaque removal and gingivitis records between waxed and unwaxed dental flosses. In 1970 O'Leary and Hill et al. in 1973 they found no difference in the interproximal cleaning properties of waxed or unwaxed dental floss. This was later reconfirmed in 1982 by Lobene et al. (Clinical Preventative Dentistry, January-February (1982)) who demonstrated that there is no significant clinical difference in plaque and gingivitis records. Similar results, ie, no clinical difference between waxed and unwaxed silks with respect to reduced gingival inflammation are shown by Finkelstein in 1979 (J. Dent, Res .. vol 58, pp 1034-1039 (1979)). No difference is shown in gingival health by Wunderlich in 1981 (J. Dent. Res .. vol 60A, p.862 (1981)). No difference in plaque removal is reported by Schmidt et al. in 1962 (J. Dent. Res .. (1962)) with silks of various types. Stevens in 1980, studied silk with variable diameters and showed no difference in plaque and gingival health. Cárter et al., Va Dent. J .. vol 52, pp. 18-27 (1975), studied waxed and unwaxed silks administered professionally and by himself and found that both significantly reduce gingival bleeding of interproximal and gingival sulci. Non-waxed silk seems to be slightly, but not significantly more effective. In view of these clinical work, it is not surprising that most of the dental flosses sold today are tied and / or waxed. The "ligament" in the weaving industry today is used more to facilitate the process and production during the manufacture of silk and packaging than for reasons of "sedatives". Since clinical trials show no difference between waxed and unwaxed silks, the silk industry has been quiet with the trend of the fabric industry to employ silk-binding agents. In any event, most people in the world do not use silk on their teeth. Instead, toothpicks or toothpicks are often used to clean your teeth. Maetani et al, in U.S. Patent No. 2,504,228 discloses a metal dental moldable coating with a PTFE coating. The PTFE coating is applied from a solution. The PTFE can also be applied to a suspension (an organosol) which can include other resins as well, such as, for example, a silicone. Lorch, in U.S. Patent No. 4,776,358 describes a silk ribbon that carries its own supply of a toothpaste. The tape can be made from a confronting pair of laminated films that are microporous. The toothpaste is placed between the confronted surfaces of the two sheets and the opposite longitudinal edges of the two sheets are sealed together. In the use of toothpaste it flows out through the pores of the sheets. The sheets can be PTFE films. The toothpaste is a conventional material, usually a commercially available material.

Blass, in the United States Patent No ~. No. 4,996,056 describes the coating of a silk or dental tape with a mixture of wax and a PTFE powder. La Rochelle, in U.S. Patent No. 4,157,386 discloses a tablet which covers the surfaces of the teeth and which contains fluoride ion, a polishing agent, and a vegetable oil. Gaffar et al, in U.S. Patent No. 5,344,641 discloses a toothpaste containing an antibacterial agent, an improved antibacterial agent, a polishing agent and a solubilizing agent. The improved antibacterial agent is a material that forms an anionic film that is thought to bond to the surface of the tooth thereby preventing bacterial attack and elevating the supply of antibacterial agent to tooth surfaces. Raaf et al, in U.S. Patent No. 4,169,885 discloses a filled capsule which has an outer hydrophilic active substance and an inner core containing a hydrophobic substance, a fluoride source and an antimicrobial substance. On the consumption of the capsule, the hydrophilic substance is believed to bind the hydrophobic active substance to the teeth. Hill et al., In the United States Patent No. 5,165,913 describes dental floss which contains a surfactant, silicone and a chemotherapeutic agent. The therapeutic agent is distributed over the spread of the silk. The surfactant and silicone are believed to cover the teeth, providing a uniform sense to the user, and preventing the attack of the bacteria. Chang, in the Reissued State Patent United No, 31,787 describes a toothpaste that reduces elution that contains a material that forms a membrane. The application of the membrane-forming material is believed to inhibit the elution of a previously applied therapeutic agent, (i.e., fluoride). Curtis et al., In U.S. Patent No. 4,528,182 and Crawford et al., In U.S. Patent No. 4No. 490,353 disclose an antiplaque dentifrice composition containing a quaternary ammonium compound, a betaine surfactant, polyethylene glycol and an abrasive. The presence of the betaine surfactant is believed to increase the dentifrice foam and prevent the deactivation of the quaternary ammonium compound. However, none of these methods have proven to be satisfactory. In this way, there remains a definite need in the art to improve methods, compositions and dental distribution systems which are effective for the prevention of bacterial adhesion to teeth and exhibit antimicrobial properties.

There also remains a need for compositions which can be effectively applied to the teeth using a toothpick or dental bars and which result in improved antimicrobial properties. Accordingly, it is an object of the present invention to provide a novel dental delivery system which exhibits improved antimicrobial properties. It is another object of the present invention to provide novel dental flosses which exhibit improved antimicrobial properties. It is another object of the present invention to provide novel toothpicks which exhibit improved antimicrobial properties. It is another object of the present invention to provide a method for treating teeth, which confers improved microbial resistance on the teeth. It is another object of the present invention to provide a method for treating teeth, which confers prolonged microbial resistance on the teeth. It is another object of the present invention to provide a method for treating teeth which results in a reduced ability of the bacteria to adhere to the teeth.

It is another object of the present invention to provide novel compositions which impart improved microbial resistance to teeth. It is another object of the present invention to provide novel compositions, which confer prolonged microbial resistance to the teeth. It is another object of the present invention to provide novel compositions, which result in a reduced ability of the bacteria to adhere to the tooth. It is another object of the present invention to provide novel cationic surfactants useful in such methods, compositions, and dental delivery systems. It is another object of the present invention to treat / cover dental surfaces with a hardened, inert, continuous, hydrophobic material, which constitutes a physical barrier against access to the tooth surface of bacteria, acids, remnant foods, etc .; and prevent the loss of fluoride by elution of dental surfaces. It is another object of the present. invention provide such barriers, by deposition on dental surfaces, which include materials, which can improve the purposes of oral hygiene such as fluoride sources, substances which show inhibit the attack, spread, growth or colonization of undesirable bacteria, Antiseptic or antibiotic materials, detergents, anti-inflammatories and other active agents. These and other objects, which will be more apparent during the following detailed description, have been achieved by the discovery of the inventors of the application of a composition which comprises: (a) from 1 to 20% by weight, based on the total weight of (a) and (b) of a transfer agent; and (b) from 80 to 99% by weight, based on the total weight of (a) and (b) of a barrier material for the teeth resulting in a prolonged reduction in the ability of the bacteria to adhere to the teeth. In this way, the present invention provides new compositions which are attached to substrates, especially those dental surfaces (teeth), which have pits, fissures, depressions, fractures, dental tubules, interstices or irregularities. The compositions according to the topography of the surfaces of the teeth, which deposit protective barrier materials on the surfaces of the teeth. The methods of this invention result in the attachment of waxy materials to substrates, such as teeth. The application of the present compositions to dental floss or dental tape, according to the methods of the present invention, provides an appropriate combination of bonding to silk or tape together with the transferability of the compositions on and towards the surfaces of the teeth. during the use of the tape or silk. The compositions of the present invention can be applied to tooth surfaces using toothbrushes, both manual and automated, which have both "natural" bristles or nylon or other fibers, multifilaments or monofilaments. The methodology used to apply the barrier materials and the duplex films to the bristles can be as described below as it is used for the application to silks and dental tapes. The compositions of the present invention can also be applied to dental surfaces using any variety of interdental or dental devices of wood, plastic, metals, etc. A device similar to a bar may be covered at one or both ends with any material suitable for coating with the composition of the present invention. The device may be similar to the interdental devices presented in the market by Johnson & amp;; Johnson known as "Sti udents", in a configuration similar to the popular cotton Q-Tips, or in the configuration in which the applicator is inserted into or otherwise attached to an appropriate fastener. The materials used to cover the ends of the device applicator may include, for example: a) natural or synthetic yarns, filaments, or other fibrous materials as well as those assembled as textiles, or for any cord material, braiding, spinning, not spinning , woven, caked, flocked, etc., in which the materials of the composition of the present invention (referred to herein as MCPI) are held between the fibers or braids of the materials; b) porous or foam-like materials in which the MCPI is held between the pores or openings; or c) non-porous, non-fibrous materials such as some types of wool, plastic, metal, etc. In the following examples, the surfaces of wooden toothpicks are coated and an MCPI film transferred to the wet surfaces of microscopic glass guides. The toothpicks are merely submerged and dried, using the same techniques as for dental floss. Thus, in one embodiment of the present invention, the surfaces of the teeth are coated with a material which forms a "duplex film" composed of a monolayer of electrostatically very strong adhesive of a positively charged polyolelectrolyte (such as, for example, , polyethyleneimine, PEI) reacted with a monolayer of fatty acid molecules. The fatty acid molecules bind to the PEI layers with their carboxylic groups while the hydrocarbon portions of the fatty acid chains form a highly hydrophobic interface that is compatible with the hydrophobic barrier materials. In addition to the fatty acids, other compounds having low surface tension and water repellent properties that can be employed in the practice of the present invention include polymethylalkysiloxanes such as, for example, polymethylhexadecylsiloxane, and polyfluoroalkylmethylsiloxanes (eg, polymethyl-3). , 3, 3-trifluoropropyl-siloxane). This additionally increases the hydrophobicity of the duplex films and facilitates the transfer of the hydrophobic barrier materials. Saturated hydrocarbons such as waxes, which include beeswax, carnauba wax and petroleum waxes such as paraffins, and fluorocarbon polymers can also be employed. In other applications, the duplex film can be replaced by a single monolayer composed of a low molecular weight surfactant in which positively charged groups react with the surfaces of the teeth and the water repellent portions of the chain form a highly hydrophobic interface. Examples of such surfactants are cetyltrimethylammonium bromide (C ) hexadecyltrimethylammonium bromide (HD ) and various amines and quaternary amines, of which a good example is the quaternary amine Hyamine-1622. The compositions of the present invention are materials generally in the solid or semi-solid state which can be applied to dental surfaces by dental floss, dental tape, interdental devices, cotton swabs, bars, toothpicks and other applicators or methods of application by the dentist. which solid or semi-solid materials can be brought into contact with tooth surfaces. Such applicators or methods of application are mentioned later referred to as "Applicators". As shown in the schematic illustrations given in Figures 1 and 2a and b, the compositions of the present invention, as applied to dental surfaces, provide a multi-stratus protective coating (hereinafter referred to as "protective coating: or "PC"), as follows: (1) The layer of the transfer agent that has double functionality, is composed of materials that have some molecular segments or parts of a polymer chain which is positively charged and other segments which exhibit characteristics hydrophobic Three categories of transfer agent materials include: (a) monomeric cationic surfactants, (b) cationic polyelectrolytes or their products or complexes with organic or inorganic acids, and (c) polypeptide-like materials that have a preponderance of positively charged functional groups. . (2) The barrier layer: for the hydrophobic components of the transfer agent layer, a hydrophobic, inert material (hereinafter referred to as a "barrier" material), such as a wax adheres. The thickness of the barrier layer is typically between lμ and approximately 10μ. In the preferred embodiments of PC they may additionally provide: (3) The antibacterial function: Within the barrier layer, therapeutically, hygienically or otherwise desirable materials may be mixed which are released as soon as they are exposed on the surfaces of the barrier layer. One of the materials typically mixed in the barrier material is a substance or substances that show inhibit attack or otherwise stop the spread, growth or colonization of harmful bacteria such as Streptococcus mutans, S. sobrinus, etc. As indicated above the composition may additionally comprise other active agents. Such substance will be referred to hereinafter as "Active Agent" or "A-A" material. In this way, the present invention makes possible the first significant improvement in consumption or dental care in the home in decades. Specifically, the present invention provides the following advances: I. The application of a composition of the present invention to the teeth provides a continuous, hydrophobic, inert barrier which prevents acids, corrosive materials, (Figure 9 shows various corrosive materials on a surface not treated on the left side, 9a compared to the same materials on the surface treated with a composition of the present invention on the right side, 9b), food particles, bacteria and other materials that gain access to the treated dental surface and thus provide protection against all the usual destructive processes - including the loss of fluoride by elution. In addition, these harmful substances do not easily attack the barrier as they would to the surface of the unprotected tooth. II. Any bacteria or other residue which attacks the protective barrier is easily removed by brushing teeth, cleaning with water pressure, silks and even, probably by rigorous mouth rinsing as the amorphous barrier is easily penetrated or cut, removing the more exterior material but removing something from its remaining protection barrier. Without such protection, the bacteria which have attacked by themselves to the surface of the tooth soon become impossible to dislodge by brushing teeth or with silks and must be professionally removed. Since the bacterial attack begins to take place after each meal, the barrier is of greater prophylactic significance. III. The barrier material easily fills and thus seals holes, fissures and fractures, which are the favorite competition for bacterial colonization and plaque development. The barrier remains in place until it is mechanically removed from these holes, etc. and therefore provides protection which is still more widespread in vulnerable areas, since the barrier material is not removed from holes, cracks, etc. As easily as from the surface of uniform teeth in the ordinary course of abrasive action by the tongue, food chewing, brushing of teeth, etc. IV. By the addition to the barrier composition of an antibacterial material, 5-amino-1, 3-bis (2-ethylhexyl) -5-methylhexahydropyrimidine, which is obtained from Angus Chemical Co, under the trade name of Hexetidine, being a example of a more especially preferred active agent, bacterial attack on the barrier surface is reduced by an estimated 90% or more, compared to the number of bacteria density which attack the surface of unprotected teeth. Of course, these bacteria which make the attack, are easily removed by the typical customary activities such as brushing teeth and silk. In addition, hexetidine appears to migrate or diffuse from the barrier material to the tooth surface to which the barrier does not reach, providing some protection to these more vulnerable areas that are difficult to reach. V. Of importance, the benefits of the present invention can be provided by a wide range of application methods, for example, silk and dental tape, Q'tips®-like cotton swabs, toothpicks, interdental devices such as Stimudents®, toothbrushes, pre-coated teeth, and any other applicators for usual or professional jobs that one wishes to use. The only criterion is that it must be able to contact a wax material to the tooth surfaces. In this way, the application of the present compositions is effective to treat / coat dental surfaces with a hard, inert, continuous, hydrophobic composition which constitutes a physical barrier against access to the tooth surface by bacteria, acids, remnant foods , etc., and prevents the loss of fluoride by elution of dental surfaces. In addition, the attack of bacteria is significantly reduced by the barrier, than the attack on unprotected tooth surfaces. More importantly, the bacteria and other materials which attack the barrier are easily removed by brushing teeth, flossing, cleaning with water pressure and even vigorous mouth rinsing since the amorphous barrier material is easily penetrated or cut with a small effort. Even after the removal of such surface materials, the barrier materials remain to continue the protection provided. One application and one subsequent, the barrier materials of the present invention are forced to conform the topography of the dental surfaces in which they will be applied. Especially important, barrier materials fill holes, fissures, fractures and other imperfections in dental surfaces, thus blocking those sites in which bacteria are most frequently found and from which it is more difficult to remove. And at such sites, barrier materials are less subject to removal by the usual oral sources of abrasion and surface activities such as tongue movements, tooth brushing, chewing, etc., and thus provide the most hardened protection where is needed In a preferred embodiment, the barrier material includes agents which improve the purposes of oral hygiene such as substances which are: (a) shown to elevate the inhibition of attack, propagation, growth or colonization of undesirable bacteria, (b) other germicidal, antiseptic or antibiotic materials, (c) anti-inflammatory and (d) other desirable agents. Using one of the preferred embodiments of the present invention, in which a material derived from heterocyclic nitroparaffins, such as hexetidine, is mixed in the barrier composition, the bacterial attack on the protected barrier is reduced by = 90% as compared to the surfaces of unprotected tooth. These few bacteria which can attack the barrier surface are removable with a gentle cutting action. BRIEF DESCRIPTION OF THE DRAWINGS A more complete appreciation of the invention and many of the concomitant advantages thereof will be readily obtained as soon as it becomes understood with reference to the following detailed description when considered together with the accompanying drawings., where : Figure 1 is a partial section, taken in a horizontal e, through a human tooth, coated, showing the surface of the irregular tooth, the conformation of the coating to the surface of the tooth and its relative thickness, all in one enlarged scale. The hydrophobic barrier film, which contains the antibacterial and other functional agents, which forms the substrate and fills the pits, fissures, fractures and other irregularities of the tooth surface. The transfer layer facilitates adhesion of the hydrophobic barrier film to the surface of the tooth; Figures 2a and b are enlarged views of the surface of the coated tooth, showing the area of the tooth surface in Figure 1, to demonstrate the distribution of electrostatic charges at the interface between the tooth surface and the transfer agent. These figures illustrate the mode of attachment of the transfer agent to the surface of the negatively charged tooth, (a) The molecules of the positively charged surfactant form a dense monolayer which binds to the negatively charged substrate. The alkyl groups of the transfer agent face away from the surface. The hydrophobic barrier film, which contains the antibacterial and other functional agents, that make up the substrate and fill the pits, fissures, fractures and other irregularities of the tooth surface. The transfer layer facilitates adhesion of the barrier film - hydrophobic to the surface of the tooth; Figures 2a and b are elongated views of the surface of the coated tooth, showing the area of the tooth surface in Figure 1, to demonstrate the distribution of electrostatic charges at the interface between the tooth surface and the transfer agent. These figures illustrate the mode of attachment of the transfer agent. to the tooth surface negatively charged. (a) The positively charged surfactant molecules form a dense monolayer which binds to the negatively charged substrate. The alkyl groups of the transfer agent face away from the surface, (b) The polyamine molecules absorbed into the substrate with their hydrophobic side groups facing away from the hydrophilic surface of the tooth; Figure 3 shows the application of a composition according to the present invention to a tooth by a cotton swab; Figures 4a and b are photomicrographs of an untreated tooth (Figure 4a) and a tooth treated according to the present invention (Figure 4b) after exposure to the bacteria-rich medium for 48 hours; Figure 5 shows the application of a composition according to the present invention to a tooth by a toothbrush; Figures 6a and b are photomicrographs of an untreated tooth (Figure 6a) and a tooth treated according to the present invention (Figure 6b) after exposure to the bacteria-rich medium for 48 hours; Figure 7 shows the application of a composition according to the present invention to a tooth by a dental floss; Figures 8a and b are photomicrographs of an untreated tooth (Figure 8a) and a tooth treated according to the present invention (Figure 8b) after exposure to the bacteria rich medium for 48 hours; and Figures 9a and b show the appearance of staining materials in an untreated glass guide (Figure 9a) and a treated guide according to the present invention (Figure 9b). Thus, in a first embodiment, the present invention provides novel compositions which contain: (a) 1 to 20% by weight, based on the total weight of (a) and (b), of a transfer agent; and (b) 80 to 90% by weight, based on the total weight of (a) and (b), of a barrier material.

Preferably, the present composition contains: (a) 3 to 5% by weight, based on the total weight of (a) and (b), of a transfer agent; and (b) 95 to 97% by weight, based on the total weight of (a) and (b), of a barrier material. THE FUNCTION OF THE TRANSFER AGENT To adhere a hydrophobic barrier material to the wet, hydrophilic, negatively charged surface of the tooth, a bifunctional transfer agent material is employed. This material has some active groups which are positively charged electrostatically and are active groups which are compatible with the hydrophobic materials of the barrier layer. Useful transfer agent materials include various compounds of cetylamines, various diamines (including, for example, Duomeens and Ethoduomeens), heterocyclic amines derived from nitroparaffins, and quaternary ammonium compounds. Also useful are the compounds of certain cationic polyelectrolytes, invented for the purposes of the present invention and introduced herein, including for example, polyethylene imine (PEI) derivatized with varying concentrations of fatty acids such as, for example, stearic acid, palmitic acid , oleic acid, etc.

Certain of these transfer agents also inhibit the attack, otherwise stop the propagation, growth or colonization of bacteria such as, for example, Streptococcus mutans and Streptococcus sobrinus, when added in appropriate concentrations to be able to function as an agent transfer and also execute the AA function. Some substances, notably some bifunctional amine hydrofluorides and specifically the quaternary ammonium fluorides, have been employed in the prior art to produce a monolayer or bipolar material that adheres to dental surfaces as well as at the end thereof. But experimentation suggests that the resulting individual molecular layer is insufficient to provide a durable functional barrier against bacterial attack or to prevent access to the tooth surface by acids, etc. Transfer Agent Materials: The cationic transfer agent materials useful in the present invention are believed to bind to the surface of the tooth by a complex interaction between the cationic portion of the material and the protein portion of the tooth and of the tooth. The shape predisposes or conditions the surface of the tooth in such a way that a waxed material will then adhere to the surface. The surface active materials which are capable of binding strongly to negatively charged and hydrophilic surfaces of human teeth include various compounds alkylammonium branched, cyclic alkylammonium compounds, petroleum derived cationic materials, and polymeric cationic materials. a) The branched-chain aquilamonium compounds R '* R "R' R-N 1 -R» R-N + -H X "R-N i + -R" X "I I R" R "' R represents a long alkyl chain (CQ.Q), which can be substituted with one or more hydroxy groups, R ', R "and R"' each independently can be both a long alkyl chain (Cg_2o) which it can be substituted with one or more hydroxy groups or small alkyl groups (C? _4), which can be substituted with one or more hydroxy groups or aryl groups (Cg_10)? hydrogen, and X "represents an anion such as chlorine or These schematic formulas are given for the purposes of defining the classes of compounds and represent the simplest concepts of cation transfer agents in which one or more hydrophobic alkyl groups are attached to the nitrogen atom.In many cases the bond is more complex , as for example, in RCONHC ^ C ^ C ^ NtC ^) 2 • In addition, the cationic transfer agents may contain more than one cationic nitrogen atom such as the following classes of compounds RNHCH2CH2CH2NH2 and derivatives of the Representative examples of compounds according to the above formulas are: cetyltrimethylammonium chloride (C ), hexadecyltrimethylammonium bromide (HD ), stearyldimethylbenzylammonium chloride, lauryldimethylbenzylammonium chloride, cetyldimethylethylammonium halide, cetyldimethylbenzylammonium halide, cetyltrimethylammonium halide, halide of dodeciletildimetilamonio halide, lauryl trimethylammonium halide cocoalquiltrimetilamonio halide, N, N-Cg_2A-dialkyl, and specifically compounds such as bis (hydrogenated seboso alkyl) dimethylammonium which is known to be absorbed on the surface with hydrophobic groups oriented away it chloride, 2-hydroxydodecyl-2-hydroxyethyl-dimethylammonium and dihydrofluoride N-octadecyl-N, N ', N'-tris- (2-hydroxyethyl) -1, 3-diaminopropane. b) Cyclic alkylammonium compounds A more preferred group of the compounds of the present invention which have been found to be applicable include a class of active surface quaternary ammonium compounds in which the nitrogen atom bearing the cationic charge is part of a heterocyclic ring. Suitable compounds, for example, are as follows: laurylpyridinium chloride or bromide, tetradecylpyridinium bromide, halide (chloride, bromide or fluoride) of cetylpyridinium. c) Petroleum-derived cationics Typical basic amines are derived from petroleum-based raw materials, such as olefins, paraffins, and aromatic hydrocarbons and include compounds with at least one aliphatic carbon chain containing six or more carbon atoms. attached to hydrogen. In this way, the salts amines, diamines, amidoamines, alkoxylated amines and their respective quaternary salts are applicable. Preferred compounds of this type include coconut or substituted sebaceous alkyls of 1,3-propylenediamines sold by Witco under the tradename of "Adogen" and "Emcol" and similar diamines sold by Akzo under the trade name "Duomeen" and its derivatives polyethenoxy under the trade names of "Ethomeen" and "Ethoduomeens". d) Polymer Amines Suitable polymer amines comprise a class of polymers that contain ionic groups along the main chain and exhibit properties of both electrolytes and polymers. These materials contain nitrogen, of primary, secondary, tertiary or quaternary functionality, in their main column and can have an average weight of molecular weights as low as approximately 100 or as high as approximately 100,000. Representations of these cationic, polymeric transfer agents are the following: polydimeryl polyamine (General Mills Chemical Co.), polyamide (trade name "Versamide"), polyacrylamides, polydiallyldimethylammonium chloride ("Cat-Floc"), polyhexamethylene biguanide compounds under the tradename "Vantocil", and also other biguanides, for example those described in U.S. Patent Nos. 2,684,924, 2,990,425, 3,183,230, 3,468,898, 4,022,834, 4,053,636 and 4,198,425, 1,5-dimethyl-1-polymethyl bromide , 5-diazaundecamethylene ("Polybrene" from Aldrich), polyvinylpyrrolidone and its derivatives, polypeptides, poly (allylamine) hydrochloride, polyoxyethylene amines and specifically polyethyleneimine ("Polymin" from BASF), and a class of related and cationic active surface polymers prepared by converting a fraction of the amino groups to their acyl derivatives. The polyethyleneimine is first condensed with less than the stoichiometric amount of the acid halides in this way by alkylating some of the amino groups and the remaining amino groups are then condensed with hydrogen halides such as hydrogen chloride or, preferably, hydrogen fluoride. The surface activity of these compounds varies with the number of amino groups which are acylated, and with the chain length of the RCO- acylating group. The condensation reaction is typically carried out with oleic or stearic acid chlorides in the presence of a solvent containing metal fluoride, preferably silver fluoride, such that the silver chloride formed in the reaction precipitates from the solvent ( see Example XV). Also suitable, for the purpose of the invention, cationic derivatives of polysaccharides such as dextran, starch or cellulose, for example, diethylaminoethyl cellulose ("DEAE-cellulose"). Examples of applicable copolymers based on acrylamide and a cationic monomer are commercially available under the tradename RETEN from Hercules Inc., or under the name of FLOC AID from National Adhesives. Particular examples of such polymers are FLOC AID 305 and RETEN 220. Similarly useful. are polyelectrolytes based on acrylamine as sold by Allied Colloids under the name PERCOL. Further examples of suitable materials are cationic guar derivatives such as those sold under the tradename JAGUAR by Celanese-Hall. A further preferred group of compounds which comprise a class of water insoluble polymers, which have nitrogen atoms in their molecules, are quaternary quaternary ammonium type, betaine type, pyridylpyridinium type or vinylpyridinium type polymers. Examples are as follows: poly (vinylbenzylmethylamylammonium chloride), poly (vinylbenzyltearylbetaine), poly (vinylbenzylurilpyridylpyridinium chloride), poly (vinylbenzylcetylammonylhexyl ester) and quaternized polyhoxyethylenated long chain amines with the formula general RN (CH3) [(C4H40)? H] 2 (+) A (-), where A (-) is generally chlorine or fluorine, x is a number from 1 to 20 and R is Cg_22 alkyl- These cationic materials , reacting with dental surfaces, produce strongly hydrophobic films in which hydrophobic barrier materials are easily transferred by spreading, rubbing or polishing.

It is important that the reason for this transferability be understood. The surfaces of human teeth are normally hydrophilic, negatively charged, and are "lubricated" by a hydrated biological film composed of bacteria and other biological organisms. The transfer and adhesion of the barrier materials on such dental surfaces is difficult or practically impossible unless the biological film is modified by a material that is hydrophobic and therefore compatible with the barrier materials. In a preferred embodiment, the transfer agent, a cationic surfactant, is a polymer which contains a nitrogen atom in a repeating unit and in which a portion of the nitrogen atoms are quaternized by formation of a salt with a fatty acid of Cg_2Q 'preferably a C12_2Q fatty acid. Examples of such polymeric cationic surfactants include polyacrylamides, polyvinylpyridines, or polyamines, for example, poly (ethyleneimine), in which from 5 to 95% mol, preferably 40% 60% per mole of nitrogen atoms that have been quaternized by the formation of a salt with a fatty acid. Typically such polymers will have an average molecular weight weight of 600 to 60,000, preferably 600 to 1,800.

In a particularly preferred embodiment, the cationic surfactant is a polymer which contains a nitrogen atom in a repeating unit and in which a first portion of the nitrogen atoms are quaternized with a Cg_2o fatty acid, preferably a fatty acid of C12_20 'and a third (3rd portion of the nitrogen atoms are quaternized to form a salt with HF. Examples of such polymeric cationic surfactants include polyacrylamides, polyvinylpyridines or polyamines, for example, poly (ethylene imine), in which from 5 to 95 % by mole, preferably from 40 to 60% by mole, of the nitrogen atoms are converted to their acid derivatives by reaction with oleic or stearic acid chlorides, and from 5 to 95% by mole, preferably from 40 to 60. % per mole of the nitrogen atoms quaternized with HF In this case, the polymeric cationic surfactant will have an average molecular weight of 600 to 60,000, preferably 600 to 1800. In another preferred embodiment, the cationic surfactant is an alkylamine of Cg_2o which has been quaternized with HF, such as cetylamine hydrofluoride. THE BARRIER FUNCTION Now having a mechanism for adhering a protective, hydrophobic material to the hydrophilic dental substrate, any of the various barrier materials can be selected to perform this function. A microcrystalline wax, for example is a component in a barrier composition which provides an adherent, conformable, hydrophobic, continuous, inert, colorless or with a little color barrier, which is an application and with subsequent rubbing or alteration is forced to the pits, fissures, fractures and other irregularities of the surface of the tooth, thus blocking these most vulnerable sites for occupation by bacteria and other undesirable residues. This wax barrier seems to last in place and function indefinitely or until it is removed mechanically. In this way, with the transfer and barrier functions performed, the extended protection is provided against harmful activities since the treated dental surfaces are entirely sealed against bacteria, acids, staining materials, loss of dental fluoride, etc. In the use, the barrier material is rubbed, in the application and after it, in the holes, fractures, concavities and other depressions. Of importance, the barrier materials are amorphous materials with cut or easily penetrated in such a way that the materials which can adhere to the surface of the barrier can be easily removed by the application of moderate cutting forces such as those applied by the tongue action against dental surfaces, brushing teeth, dental floss, vigorous cleaning of water or vigorous rinsing of the mouth. These same low-cut characteristics move the barrier materials close by exposing any active agent substance mixed in the barrier materials. Hydrophobic Barrier Materials It has been found that several hydrophobic compounds of high molecular weight, solid at body temperature and generally similar to fats and oils are useful as barrier forming materials. Typically they are long chain hydrocarbons, especially normal paraffins having a chain length of 16 carbon atoms or larger, paraffins with various branching sites and unsaturation, where the degree of such branching and unsaturation do not create unacceptable toxicity or low point of solidification below the body temperature, and shows essentially no solubility in water or saliva. The major types of these wax-like materials fall into two basic categories: I. Natural waxes of animal, vegetable or mineral origin, such as beeswax, lanolin, sperm, carnauba wax, petroleum waxes including paraffin waxes and microcrystalline petrolatum; and II. Synthetic materials including ethylene polymers such as "Carbowax" polymethylene wax ("Paraflint") and various types of hydrocarbons as obtained by the Fisher-Tropsch synthesis. Other suitable materials include silicone-based polymers such as polymethyl alkylsiloxane, polydimethylsiloxane, poly (perfluoroalkylmethylsiloxane), poly (methyl-3,3,3-trifluoropropylsiloxane), and various aromatic siloxanes (containing phenyl) and are sold by Petrarch, which is now United Chemical. Also useful are various fluoropolymers where some or all of the hydrogens are replaced by fluorine, which include, among others: polytetrafluoroethylene (PTFE); fluorinated polyethylene-propylene (FEP); polyvinylidene fluoride (PVDF); and polyvinyl fluoride (PVF). These polymers can be applied to dental devices such as aqueous or non-aqueous dispersions. In another embodiment, the present composition contains: (a ') 1 to 10% by weight, preferably 2 to 5% by weight, based on the total weight of (a1), (b') and (c ') of a transfer agent; (b1) 70 to 98% by weight, preferably 85 to 93% by weight, based on the total weight of (a1), (b ') and (c') of a barrier material; and (c1) 1 to 20% by weight, preferably 5 to 10% by weight, based on the total weight of (a1), (b ') and (c') of an active agent. THE FUNCTION (A-A) OF THE ACTIVE AGENT The experiment with the technology of the present invention demonstrates that some types of materials inhibit or stop the attack and / or propagation, growth or colonization of bacteria on dental surfaces. The bacteria with which the experiments were carried out, Streptococcus mutans, and Streptococcus sobrinus, show to be the majority sources of bacterial plaque colonies and their sequelae. Among the materials which demonstrate performing the A-A function are various cetyl inas, nitroparaffin derivatives, duomeens, ethoxylated duomeens, and other quaternary ammonium compounds. Especially useful is 5-amino-1,3-bis (2-ethylhexyl) -5-methylhexahydropyrimidine, such as that obtained from Angus Chemical Co. under the tradename hexetidine. In addition, innovative materials whose benefits and novel compositions are described and claimed for the first time in this description / application are useful as Active Agents. These include polyethyleneimines for which fatty acids such as oleic acid, etc., have been added.Some of the AA materials tested and described in the examples below migrate outward or diffuse away from the areas in which a Protective Coating is applied in such a way that, to some extent, the AA function extends to areas not reached by PC by itself. These materials A-A can be mixed in the barrier material in such a way that, as the barrier material is cut, penetrates, disturbs, erodes, abrades, etc., fresh A-A material is exposed and free to function. Active Agent Materials Various compounds which possess antibacterial activity (i.e., are germicidal) can be employed in compositions of the present invention to counteract bacterial attack and plaque formation. Examples of applicable antimicrobial agents belong to the following types. a) Halogenated salicylanilide free amine compounds, such as those described in U.S. Patent No. 5,344,641, which include: 4 ', 5-dibromosalicylanilide, 3,4', 5-trichlorosalicylanilide, 3,4 ', 5-tribromosalicylanilide , 2,3,3 ', 5-tetrachlorosalicylanilide, 3,3,3', 5-tetrachlorosalicylanilide, 3,5-dibromo-3 '-trifluoromethyl salicylanilide, 5-n-octanoyl-3' -trifluoromethyl salicylanilide, 3, 5 -dibromo-4 '-trifluoromethyl salicylanilide, 3,5-dibromo-3'-trifluoromethyl salicylanilide (fluorophen) Benzoic Esters Methyl Ester p-hydroxybenzoic Ethyl Ester p-hydroxybenzoic Propyl Ester p-hydroxybenzoic Butyl Ester p-hydroxybenzoic halogenated diphenylethers, such as those described in U.S. Patent No. 5,344,641, which include: 2 *, 4, 4'-trichloro-2-hydroxy-diphenyl ether (Triclosan) 2 ', 2'-dihydroxy-5, 5 '-dibromo-diphenyl ether. halogenated carbanilides as described in U.S. Patent No. 5,344,641, which includes: 3,4,4'-trichlorocarbanilide, 3-trifluoromethyl-4,4'-dichlorocarbanilide, 3,3,4'-trichlorocarbanilide. Also included are phenolic compounds, representative examples of which are described in U.S. Patent No. 5,290,541, which include phenol, its derivatives and biphenol compounds Specifically include: Phenol and its Homologs Phenol -Fenol 2 methyl-Phenol 3 methyl-Phenol 4 methyl-Phenol 4 ethyl-Phenol 2,4-dimethyl-Phenol 2,5-dimethyl-Phenol 3,4-dimethyl-Phenol 2,6-dimethyl-Phenol 4-n -propyl -Fenol 4-n-butyl -Fenol 4-n-amyl -Fenol 4-ter-amyl -Fenol 4-n-hexyl -Fenol 4-n-heptyl -Fenol 2-methoxy-4- (2-propenyl) -phenol (Eugenol) 2-isopropy1-5-methy1-phenol (Thymol) Halofenols of mono and polyalkyl and aralkyl methyl-p-chlorophenol ethyl-p-chlorophenol n-propyl • p-chlorophenol n-butyl-p-chlorophenol n-amyl-p-chlorophenol sec-amyl-p-chlorophenol n-hexyl -p-chlorophenol cyclohexyl: p-chlorophenol n-heptyl -p-chlorophenol n-octyl-p-chlorophenol O-chlorophenol methyl -p-chlorophenol ethyl -p-chlorophenol n-propyl -p-chlorophenol n-butyl -p-chlorophenol n-amyl -p-chlorophenol ter-amyl -p-chlorophenol n-hexyl -p-chlorophenol n- heptyl -p-chlorophenol p-chlorophenol o-benzyl-p-chlorophenol o-benzyl-m-methyl -p-chlorophenol o-benzyl-m, m-dime yl -p-chlorophenol or -phenylethyl -p-chlorophenol or -phenylethyl -m-methyl-p-chlorophenol 3-methyl-p-chlorophenol 3,5-dimethyl-p-chlorophenol 6-ethyl-3-methyl-p-chlorophenol 6 -. 6-n-propyl-3-methyl-p-chlorophenol 6-iso-propyl-3-methyl-p-chlorophenol 2-ethyl-3, 5-dimethyl-p-chlorophenol 6-sec-butyl-3-methyl-p-chlorophenol 2-iso-propyl-3, 5-dimethyl-p-chlorophenol 6-diethylmethyl-3-methyl-p-chlorophenol 6-iso-propyl-2-ethyl-3-methyl-p-chlorophenol 2-sec-amyl-3, 5-dimethyl-p-chlorophenol 2-diethylmethyl-3, 5-dimethyl-p-chlorophenol 6-sec-octyl-3-methyl-p-chlorophenol p-bromophenol methyl -p-bromophenol ethyl -p-bromophenol n-propyl-p-bromophenol n-butyl -p-bromophenol n-amyl -p-bromophenol sec-amyl -p-bromophenol n-hexyl-p-bromophenol cyclohexyl-p-bromophenol ter-amyl-p-bromophenol n-hexyl-p-bromophenol n-propyl-mm-dimethyl 2-phenyl phenol 4-chloro-2-methyl phenol 4 -chloro-3-methyl phenol 4-chloro-3,5-dimethyl phenol 2,4-dichloro-3,5-dimethyl phenol 3,4,5,6-tetrabromo-2-methyl phenol 5-methyl-2-pentylphenol 4-isopropyl-3-methylphenol 5-chloro-2-hydroxydiphenylmethane Resorcinol and its derivatives resorcinol-resorcinol methyl-resorcinol ethyl-resorcinol n-propyl-resorcinol n-butyl-resorcinol n-amyl-resorcinol n-hexyl-resorcinol n-heptyl-resorcinol n-octyl-resorcinol n-nonyl-resorcinol phenyl-resorcinol benzyl-resorcinol phenylethyl -Resorcinol phenylpropyl -Resorcinol p-chlorobenzyl -Resorcinol 5-chloro-2,4-dihydroxydiphenyl methane 4'-chloro -2,4-dihydroxydiphenyl methane -bromo -2,4-dihydroxydiphenyl methane 4 '-bromo -2, 4-dihydroxydiphenyl methane Bisphenol A 2 (2'-methylene bis (4-chlorophenol) 2,2'-methylene bis (3,4,6-trichlorophenol) (hexachlorophenol) 2,2'-methylene bis (4-chloro-6-bromophenol) sulfide of bis (2-hydroxy-3, 5-dichlorophenyl) sulfide of bis (2-hydroxy-5-chlorobenzyl) b) Amine-containing compounds (most quaternary amines) Among the most common antibacterial quaternary ammonium compounds are: alkyldimethylbenzylammonium benzethonium chloride (Hyamine 1622), diisobutylphenoxyethoxyethyl ethyl dimethyl benzyl ammonium chloride and cetylpyridinium halides (chlorine, bromine, iodine, and fluorine). Other materials of this nature are also mentioned in: U.S. Patent Nos. 2,984,639, 3,325,402, 3,431,208, and 3,703,583 and British Patent No. 1,319,396. Further analogous compounds include those in which one or two of the substituents on the quaternary nitrogen have a chain length of carbon atoms (typically alkyl groups) of 8 to 20, typically 10 to 18, carbon atoms while the Remaining substituents have a low number of carbon atoms (typically alkyl or benzyl groups), such as from 1 to 7 carbon atoms, typically methyl or ethyl groups. Typical examples are: dodecyltrimethylamine bromide and benzyldimethylstearylammonium chloride. The preferred antimicrobial materials employed in the present invention pertain to the heterocyclic class compounds derived from nitroparaffins. Examples of such compounds can be classified into the following types: monocyclic oxazolidines, bicyclic oxazolidines, bicyclic polymeric oxazolidines, oxazalines 1-3-dioxanes, oxazolidinones, and hexahydropyrimidines [5-amino-1,3-bis (2-ethylhexyl) -5) -methyl hexahydropyrimidine which is sold under the trade name of "hexetidine" by Angus Chemical Co.], Other antimicrobial substances based on guanine are: 1,6-bis- (p-chlorophenyldiguanidine) hexane, also known under the trade name of "chlorohexidine", 1,6-di- (2-ethylhexildiguanidina) hexane, known as "alexidine", and 1,1 '-hexamethylene-bis-. { 5- (4-fluorophenyl) -diguanidine} also known as "fluorhexidine", In a preferred embodiment of this invention, a non-aqueous dispersion containing microcrystalline wax, paraffin oil and hexetidine is prepared. The resulting mixture is applied to a polyamide dental tape by spreading the tape through the dispersion. After drying, the tape extends over the extracted teeth of humans and the glass rollers. The test and the observation show that a substantial, uniform and continuous coating of a waxed barrier film has been applied to both surfaces of the teeth and the glass rollers. The film is also transferred when the dental and glass surfaces are moistened with water immediately before the treatment. Hydrophobic films of applied materials are not removed by brushing with ten strokes of the toothbrush while submerging in the water. As indicated above, the present compositions may further comprise a source of fluorine, such as sodium fluoride, potassium fluoride, tin fluoride, zinc fluoride, organic fluorides such as long chain aminofluorides, for example oleylamino fluoride, cetylaminofluoride or ethanolaminohydrofluoride, fluorosilicates, for example, potassium hexafluorosilicate or sodium hexafluorosilicate, fluorophosphates such as ammonium, sodium, potassium, magnesium or calcium fluorophosphate and / or fluorozirconates, for example sodium, potassium and tin fluorozirconate. The present compositions may also further comprise one or more antibiotics, such as penicillin, polymyxin B, vancomycin, kanamycin, erythromycin, nidamycin, metronidazole, spiramycin and tetracycline. The present compositions can be prepared by a method in which the barrier material is first suspended or dissolved in an appropriate solvent (for example, xylene, toluene, petroleum ether, methanol, ethanol or where, for example, aqueous dispersions of fluorocarbons are selected as barrier materials, water). The transfer agent and, optionally, active agents are then added and the solvent removed by, for example, evaporation. The present dental delivery systems can be prepared by coating a suitable substrate (dental floss, toothbrush, toothpick, etc.) with the composition present. This can be conveniently carried out by immersing the substrate in the suspension or solution containing the barrier material, transfer agent, and optionally active agent referred to above in connection with the preparation of the present compositions, and then drying the substrate to remove the solvent, leaving a coating of the present composition on the substrate. Alternatively, the dry composition prepared above can be redissolved or resuspended, and the substrate immersed in the solution or suspension formed in this way, followed by removal of the solvent. The present method of protecting the teeth can be carried out by contacting the dental distribution system with the teeth to effect the transfer of the composition of the dental distribution system to the surface of the teeth. The exact means of contacting will of course depend on the nature of the dental distribution system. In this way, in the case of a dental floss, passing the silk will suffice, while brushing will suffice, in the case of a toothbrush. Rubbing will be appropriate for both toothpicks and cotton swabs. Other features of the invention will become apparent in the course of the following descriptions of the exemplary embodiments which are given for illustration of the invention and are not intended to be limiting thereof.

EXAMPLES In the following examples, and in full their specifications, all parts and percentages are given by weight, and all temperatures are in degrees Celsius, unless expressly stated otherwise. Where the solids content of a dispersion or solution is reported, it expresses the weight of the solids based on the total weight of the dispersion or solution, respectively. Where a molecular weight is specified, this is the molecular weight range assigned to the product by the commercial supplier, which is identified. It is generally believed to be the average weight of the molecular weight. In all the following examples in which the teeth are mentioned, the teeth are teeth extracted from humans which are professionally cleaned with abrasives, sterilized by the auto-clave several times and, prior to their use in the following examples, hydrated in water distilled at least one hour. Immediately prior to the use of the teeth, they are submerged and removed from a mixture of distilled water and fresh human saliva (at approximately 1: 1 by volume), so that the treated surfaces are moist at the time of application of the materials. Example I: 43 grams of xylene solvent sold by EM Science, 5 grams of microcrystalline wax sold by Calwax under the trade designation of Victory White and 2 grams of paraffin oil, 340-355 Saybolt viscosity, sold by EM Science, heat to approximately 50 ° C and mix vigorously until a clear solution is produced. The mixture is allowed to cool to room temperature and 0.125 grams of N-tallow-1,3-propanediamine sold by Akzo under the trade designation of Duomeen TDO (as the transfer agent) is mixed by stirring. The result is a mixture in which the microcrystalline wax appears to be uniformly dispersed but not dissolved in the solvent. A cotton tip applicator is immersed in this mixture and the solvent is allowed to evaporate at an elevated temperature of about 50 ° C. The coated applicator is then rubbed against a tooth surface until a uniform and water-repellent film is obtained, the surface of the tooth has been moistened with 1: 1 by volume of distilled water mixture and fresh human saliva, immediately before the application of the coated applicator (see Figure 3). In order to determine the degree of hydrophobicity imparted by the waxed film, drops of water are deposited on the surface of the film and their contact angles are measured. Repeated measurements show values in excess of 90 ° C that indicate a strong tendency of the surface to repel water.

Demonstration of In Vitro Efficacy The inhibition-absorption ability of the bacterium of each formulation thus obtained is evaluated as follows: a pure culture of bacteria obtained from the American Type Culture Collection (ATCC), (designated ATCC # 27607, and identified as Streptococcus sobrinus, the same organisms that also have and have been previously designated and identified as Streptococcus mutans), are maintained by their culture on fresh brain-heart infusion agar plates and incubating in a C02 incubator at 37 ° C. To prepare a test medium, a small amount of bacteria is transferred to 4 ml of liquid brain heart infusion medium (BHI) (obtained from Curtis Matheson) and incubated for 24 hours at 37 ° C. After the incubation period the concentration of the bacteria in the inoculum is adjusted, with sterilized BHI medium, to approximately 2 x 107 cells / ml (OD560 = 0.02). The contact bacteria solution (0.3 ml) of the above is added to 30 ml of BHI medium containing 4% sucrose and which is in motion at 120 strokes / minute for 3 minutes. Test samples from the untreated teeth and teeth coated with the transfer film are placed in the inoculum medium and incubated under anaerobic conditions at 37 ° for 48 hours. After the removal of the medium, the teeth are rinsed in water and stained with the crystal violet dye. Microscopic examination reveals a significant inhibition of the adhesion of bacteria in the areas covered by the transferred films compared to the untreated control surfaces which are covered by heavy deposits of adherent bacteria. Example II: A mixture is prepared as described in Example I. A polyamide dental floss, such as that manufactured by Johnson & Johnson, Inc., is pulled through and vertically out of the mix at a rate of 3 mm per second, the thickness of the coating is controlled by the speed at which the silk passes through the mixture. Following the drying of air at an elevated temperature, a short chain of silk, approximately 2 feet long, is passed backwards and four times crosses the surfaces of the tooth (central incisors extracted from human), imitating a normal procedure of passing the silk, until a uniform and hard adherent film is produced (see Figure 7). The film exhibits a high degree of hydrophobicity as tested by measurements of contact angles in excess of 90 ° C. The adhesion of the bacteria to the surfaces of the tooth is evaluated according to the procedure indicated in Example I. Significant inhibition of the adhesion of bacteria to the transfer film is observed.

Example III: A mixture is prepared as described in Example I. The wooden toothpicks are immersed in the mixture and slowly removed. After drying at room temperature, the toothpicks are rubbed on the extracted and moistened tooth surfaces until a uniform and continuous film is formed. In addition, in order to determine the degree of hydrophobicity imparted by the waxed film, drops of water are deposited on the surface of the film. Repeated measurements of the contact angles show values above 90 ° which indicate a high degree of hydrophobicity of the interface. The exposure of the treated teeth in the bacteria medium for 48 hours or more demonstrates a significant reduction in the absorption of bacteria, comparable to the reduction observed in Examples I and II. Example IV: A mixture is prepared as described in Example I. Ordinary toothbrushes, some of which the bristles are "natural" and some nylon fibers, are immersed in the mixture and removed at a rate of about 3. mm / second. After drying at high temperature, the toothbrushes are passed several times on the surfaces of the teeth, simulating the action and movement of the tooth brushing (see Figure 5) the treated surfaces of the teeth are then observed by the microscope. Substantial, uniform and continuous layers of the deposited wax material appear on the surface of the tooth. In addition, in order to determine the degree of hydrophobicity imparted by the wax film, drops of water are deposited on the transferred films and the contact angles are measured. Repeated measurements show values above 90 ° that indicate the high degree of hydrophobicity of the surfaces. A significant inhibition of the adhesion of bacteria to the transferred film is observed. Example V: 43 grams of xylene solvent sold by EM Science, 5 grams of microcrystalline wax coming from Calwax under the trade name of Victory White and 2 grams of paraffin oil, 340-355 Saybolt viscosity, sold by EM Science. heat to approximately 50 ° C and mix vigorously until a clear solution is produced. The mixture is allowed to cool to room temperature. Then, 0.2 grams of cetylamine sold by Aldrich (as transfer agent) is mixed by stirring. The result is a mixture in which the microcrystalline wax appears to be uniformly dispersed but not completely dissolved in the solvent. The cotton end applicators are immersed in this mixture and removed, allowing the solvent to evaporate at an elevated temperature. The coated applicator is then rubbed against the moistened glass guides until a uniform and water repellent film is obtained. In order to determine the degree of hydrophobicity imparted by the wax film, drops of water are deposited on the surface of the film and the contact angles are measured. Repeated measurements show values greater than 90 ° indicating a strong tendency of the surface to repel water. The adhesion of the bacteria to the surfaces of the tooth is evaluated according to the procedure indicated in Example I. Significant inhibition of the adhesion of bacteria to the barrier film is observed. Example VI: A mixture is prepared as described in Example V. A polyamide dental floss, such as that manufactured by Johnson & amp; amp;; Johnson, Inc. is passed through and vertically out of the mixture at a rate of about 3 mm per second, the thickness of the coating being controlled by the speed at which the silk passes through the mixture. Following an air drying at elevated temperature, a short string of silk, approximately 2 feet in length, is passed and crossed over the surfaces of the teeth, imitating a process of passing the normal silk until a uniform adherent film and it lasts. The film exhibits a high degree of hydrophobicity as evidenced by measurements of contact angles greater than 90 °. The adhesion of the bacteria to the surfaces of the tooth is evaluated according to the procedure indicated in Example I. Significant inhibition of bacterial adhesion to the film is observed. Example VII: A mixture is prepared as described in Example V. Wooden toothpicks are immersed in the mixture and slowly removed. After drying at room temperature, the toothpicks are repeatedly rubbed onto the surfaces of the moistened tooth until a uniform and continuous film is formed. In addition, in order to determine the degree of hydrophobicity imparted by the wax film, drops of water are deposited on the surface of the film and the contact angles are measured. The repeated measurements show values of 90 ° C that indicate a high degree of hydrophobicity of the interface. The exposure of the treated teeth to the bacteria medium results in a significant reduction in the absorption of bacteria compared to the reduction observed in Examples V and VI.

Example VIII: A mixture is prepared as described in Example V. Ordinary toothbrushes, some of which the bristles are of "natural" fibers and some of nylon, are immersed in the mixture and slowly removed. After drying at high temperature, the toothbrushes are passed several times over the surfaces of the teeth, moistened, simulating the action and movement of tooth brushing. The treated surfaces of the teeth are then observed by the microscope. Substantial, uniform and continuous layers of the deposited wax material appear on the surface of the tooth. In addition, in order to determine the degree of hydrophobicity imparted by the wax film, drops of water are deposited on the transferred films and the contact angles are measured. Repeated measurements show values above 90 ° that indicate the high degree of hydrophobicity of the surfaces. Incubation for 48 hours in the bacteria medium shows a significant inhibition of bacterial adhesion. It is further noted that the subsequent brushing, while both teeth and toothbrushes are immersed in water, result in the complete removal of the bacteria from the wax film while around the untreated areas remain covered by the bacterial colonies.

Elevation of Bacterial Attack Inhibition and / or Propagation. Growth and Colonization: A significant elevation in the efficacy of the barrier film to inhibit the adhesion of bacterial colonies is realized when various antibacterial agents such as hexetidine, for example, are incorporated into the formulation. Examples IX to XII demonstrate the effectiveness of this method. Example IX: 43 grams of xylene solvent sold by MS Science, 5 grams of microcrystalline wax coming from Calwax under the trade designation of Victory White and 2 grams of paraffin oil, 340-355 Saybolt viscosity, sold by EM Science are heated to approximately 50 ° C and mixed vigorously until a transparent solution occurs. The mixture is allowed to cool to room temperature. Then, 0.3 grams of Duomeen TDO (AKZO Chemical Co.) (as a transfer agent) is mixed by stirring. To this mixture is added 1.25 grams of 5-amino-l, 3-bis (2-ethylhexyl) -5-methylhexahydropyrimidine sold by Angus Chemical Co., under the trade designation of hexetidine (as active agent) with vigorous mixing. The result is a mixture in which the microcrystalline wax appears to be uniformly dispersed but not dissolved. The applicator with cotton tip is immersed in this mixture and the solvent evaporates at elevated temperature. The coated applicator is then rubbed against the glass guides until a uniform and water-repellent film is obtained, the guide that has been moistened with distilled water immediately prior to application of the applicator. In order to determine the degree of hydrophobicity imparted by the wax film, drops of water are deposited on the surface of the film and the contact angles are measured. Repeated measurements show values greater than 90 ° indicating a strong tendency of the surface to repel water. The ability of the barrier film to inhibit the absorption of bacteria is evaluated as described in Example I. A negligible number of bacterial colonies, compared to the untreated control areas adjacent to the film are observed even after 4 days of exposure to the medium that has bacteria. Example X: A mixture is prepared as described in Example IX. A polyamide dental floss, such as that manufactured by Johnson & Johnson, Inc. is passed through and vertically out of the mixture at a rate of about 3 mm per second, the thickness of the coating being controlled by the speed at which the silk passes through the mixture. Following with an air drying at high temperature, a short chain of silk, approximately 2 feet in length, is passed between and back from the surfaces of the teeth, (central incisors extracted from human), imitating a normal procedure of passing the silk, until a uniform and hard adherent film is produced. The film exhibits a high degree of hydrophobicity as tested by measurements of contact angles greater than 90 ° C. The adhesion of the bacteria to the surfaces of the treated tooth is evaluated according to the procedure indicated in Example I. Examination by microscope (Figure 8a and 8b) reveal that the area covered by the transferred film is substantially free of bacterial colonies while that around untreated control areas are covered by heavy deposits of absorbed bacteria. Example XI: A mixture is prepared as described in Example IX. The wooden toothpicks are immersed in the mixture and removed. After drying at room temperature, the toothpicks are repeatedly rubbed onto the surfaces of the moistened tooth until a uniform and continuous film is formed. In addition, in order to determine the degree of hydrophobicity imparted by the wax film, drops of water are deposited on the surface of the film and the contact angles are measured. Repeated measurements show values greater than 90 ° C that indicate a high degree of hydrophobicity of the interface. The exposure of the treated teeth in the bacteria medium results in a negligible amount of colonies of isolated bacteria adhering to the surface of the film. Example XII: A mixture is prepared as described in Example IX. Ordinary toothbrushes, some of which the bristles are made of "natural" fibers and some of nylon, are submerged in the mixture and slowly removed. After drying at high temperature, the toothbrushes are passed several times over the surfaces of the teeth, moistened, simulating the action and movement of tooth brushing. The treated surfaces of the teeth are then observed by the microscope. Substantial, uniform and continuous layers of the deposited wax material appear on the surface of the tooth. In addition, in order to determine the degree of hydrophobicity imparted by the wax film, drops of water are deposited on the transferred films and the contact angles are measured. Repeated measurements show values above 90 ° that indicate the high degree of hydrophobicity of the surfaces. Incubation for 48 hours in the bacteria medium shows a high resistance of the film to react with any component of the media including bacteria (Figure 6a and 6b). Microscopic observations fail to detect any residual bacteria or bacterial colonies after the surface of the treated tooth is gently brushed with a toothbrush under running water. Example XIII: 83.5 grams of xylene solvent sold by EM Science, 10 grams of microcrystalline wax coming from Calwax under the trade designation of Victory White and 4 grams of paraffin oil, 340-355 Saybolt viscosity, sold by EM Science. heat to approximately 50 ° C and mix vigorously until a clear solution is produced. The mixture is allowed to cool to room temperature. For this mixture 2.5 g of 5-amino-l, 3-bis (2-ethylhexyl) -5-methylhexahydropyrimidine sold by Angus Chemical Co., under the commercial designation of hexetidine (as a transfer agent and active agent) is added with mixing vigorous. The result is a mixture in which the microcrystalline wax appears to be uniformly dispersed but not completely dissolved. The applicator with cotton tip is immersed in this mixture and the solvent is evaporated at high temperature (40-50 ° C). The coated applicator is then rubbed against the surfaces of the tooth until a uniform and water repellent film is obtained. In order to determine the degree of hydrophobicity imparted by the wax film, drops of water are deposited on the surface of the film and the contact angles are measured. Repeated measurements show values greater than 90 ° indicating a strong tendency of the surface to repel water. The adhesion of the bacteria to the treated surfaces is evaluated according to the procedure indicated in Example I. Microscopic examination shows that the treated surface areas of the teeth are essentially free of the absorbed bacteria while the control surfaces do not. treated are loaded with heavy deposits of colonies of adherent bacteria (Figures 4a and 4b). Example XIV: 84.75 grams of xylene solvent sold by EM Science, 10 grams of microcrystalline wax sold by Calwax under the trade designation of Victory White and 4 grams of paraffin oil, 340-355 Saybolt viscosity, sold by EM Science, heat to approximately 50 ° C and mix vigorously until a clear solution is produced. The mixture is allowed to cool to room temperature. To this mixture is added 1.25 grams of N-tallow-1,3-propanediamine diolate sold by Akzo Nobel Chemicals Inc., under the trade designation of Duomeen TDO (as a transfer agent and active agent) with vigorous mixing. The result is a mixture in which the microcrystalline wax appears to be uniformly dispersed but not completely dissolved. A cotton end applicator is immersed in this mixture and the solvent is allowed to evaporate at an elevated temperature (40-50 ° C). The cotton applicator is rubbed against a glass guide until a uniform and water-repellent film is obtained. In order to determine the degree of hydrophobicity imparted by the waxed film, drops of water are deposited on the surface of the film and their contact angles are measured. Repeated measurements show values greater than 90 ° indicating a strong tendency of the surface to repel water. The adhesion of the bacteria to the barrier film is evaluated according to the procedure indicated in Example I. Significant inhibition of the adhesion of bacteria to the barrier film is observed. Example XV: 4.3 grams of polyethyleneimine (1/10 segmental molecular weight) and 15.2 grams of stearyol chloride (1/20 moles) are dissolved in 25 ml of ethanol and brought to gentle reflux for 30 minutes. After cooling to room temperature, 25 ml of a 25% aqueous solution of silver fluoride is added and the mixture is stirred for 10 minutes. The silver chloride is removed and the unpurified derivative is purified by crystallization. The crystalline derivative is transferred to a plastic beaker and dissolved in 25 ml of ethanol. 3.0 grams of 40% hydrofluoric acid (1/20 mol + 20%) is added to the solution and the -totality is then evaporated in a water bath until its consistency is similar to a paste. The remaining solvent is removed in vacuo to about 50 ° C. The compound remains as a brown colorless paste. It is soluble in alcohols and solvents based on hydrocarbons. Obviously, numerous modifications and variations of the present invention are possible in light of the above teachings. It is therefore understood that, within the scope of the appended claims, the invention may be practiced otherwise than as specifically described herein. All patents and other references mentioned in the foregoing are fully incorporated herein, by this reference, the same as indicated.

Claims

CLAIMS 1. A composition characterized in that it comprises: (a) from 1 to 20% by weight, based on the total weight of (a) and (b) of a transfer agent; and (b) from 80 to 99% by weight, based on the total weight of (a) and (b) of a barrier material, wherein the transfer agent is selected from the group consisting of the compounds of the formula ( I), (II) and (III): R 'R' R 'RNR "RN ± HX" RN ± R »X" IIR "R"' (I) (ID (III) where R represents an alkyl chain (Cg_2o) / which can be substituted with one or more hydroxy groups, R! , R "and R" 'each independently are an alkyl chain (Cg_2o) > Which can be substituted with one or more hydroxy groups, a (C 1-4) alkyl, which can be substituted with one or more hydroxy groups, an aryl group (C 6-10 ° hydrogen, and X is fluorine or chlorine; laurylpyridinium chloride, laurylpyridinium bromide, cetylpyridinium chloride, cetylpyridinium bromide, cetylpyridinium fluoride, cationic petroleum derivatives, polydimethyl polyamines, polyamines, polyacrylamides, polydiallyl dimethyl ammonium chlorides, polyhexa ethylene biguanides, 1,5-dimethyl polymethobromide, 1, 5-diazaundecamethylene, polyvinylpyrrolidones, polypeptides, poly (allylamine) hydrochloride, polyoxyethylene amines, polyethyleneimines, acylated polyethylenimines, diethylaminoethylcellulose, poly (vinylbenzyltearylbetaine), poly (vinylbenzylmethylaurylammonium chloride; benzylauryl-pyridylpyridinium); poly (vinylbenzylcetylammonylhexylether): compound of the formula RN (CH3) [CC2HyO)? H] 2 (+) A (-), where A (-) is chloro or fluoro, X is a number from 1 to 20 and R is Cg_22 alkyl; polyacrylamide in which 5 to 95 mol% of the nitrogen atoms have been derived by reaction with a fatty acid halide of Cg_20 and 5 to 95 mol% of the nitrogen atoms have been quaternized with HF; polyvinylpyridine in which 5 to 95 mol% of the nitrogen atoms have been derived by reaction with a fatty acid halide of CQ_20 and 5 to 95 mol% of the nitrogen atoms have been quaternized with HF; and 5-amino-l, 3-bis (2-ethylhexyl) -5-methylhexahydropyrimidine; and wherein the barrier material is selected from the group consisting of beeswax, lanolin, sperm, carnauba wax, paraffin waxes, microcrystalline waxes, petrolatum waxes, ethylene polymer waxes, polymethylene waxes, polymethylalkysiloxane, polydimethylsiloxane, poly (perfluoroalkylmethylsiloxane), poly (methyl-3, 3, 3-tri-fluoropropylsiloxane), polytetrafluoroethylene, fluorinated polyethylene-propylene, polyvinylidene fluoride, and polyvinyl fluoride. The composition according to claim 1, characterized in that it comprises 3 to 5% by weight, based on the total weight of (a) and (b) of the transfer agent; and 95 to 97% by weight, based on the total weight of (a) and (b) of a barrier material. 3. The composition according to claim 1, characterized in that the transfer agent is 5-amino-l, 3-bis (2-ethylhexyl) -5-methyl-hexahydropyrimidine. 4. The composition according to claim 1, characterized in that the transfer agent is polyethyleneimine in which 5 to 95 mol% of the nitrogen atoms have been derived by reaction with a fatty acid halide of Cg_20 and 5 to 95 % in mol of the nitrogen atoms have been quaternized with HF. 5. The composition according to claim 1, characterized in that the barrier material is a microcrystalline wax. 6. A composition characterized in that it comprises: (a ') from 1 to 10% by weight, based on the total weight of (a1), (b') and (c ') of a transfer agent; (b1) from 70 to 98% by weight, based on the total weight of (a '), (b1) and (c1) of a barrier material; and (c ') 1 to 20% by weight, based on the total weight of (a'), (b ') and (c') of an active agent; wherein the transfer agent is selected from the group consisting of the compounds of the formula (I), (II) and (III): R1 R1 R 'RN IR "R-NI ± HX" R-NI ± R "X" (I) (II) (III) where R is an alkyl chain of C8_2Q, which can be substituted with one or more hydroxy groups, R1, R "and R" 'each independently are an alkyl chain of Cg_20, which can be substituted with one or more hydroxy groups, a C1-4 alkyl group, which may be substituted with one or more hydroxy groups, an aryl group of c6-10 ° hydrogen, and X is fluorine or bromine; laurylpyridinium chloride; laurylpyridinium bromide; cetylpyridinium chloride; cetylpyridinium bromide; cetylpyridinium fluoride; cationic petroleum derivatives; polydimeryl polyamines; polyamides; polyacrylamides, polydiallyl dimethyl ammonium chlorides, polyhexamethylene biguanides; 1, 5-dimethyl-l, 5-diazaundecamethylene polymethobromide; polyvinyl pyrrolidones; polypeptides, poly (allylamine) hydrochloride; polyoxyethylene amines; polyethylene imines; acylated polyethylenimines; diethylaminoethyl cellulose; poly (vinyl-benzylstearylbetaine); poly (vinylbenzylmethylaurylammonium chloride) poly (vinylbenzyluril pyridylpyridinium chloride) poly (vinylbenzylcetylmonylhexylether) compound of the formula RN (CH3) [CC2HyO)? H] 2 (+) A (-) wherein A (-) is chloro or fluoro, X is a number from 1 to 20 and R is an alkyl group of C8_22; polyacrylamide in which 5 to 95 mol% of the nitrogen atoms have been derived by reaction with a fatty acid halide of Cg_20 and 5 to 95 mol% of the nitrogen atoms have been quaternized with HF; polyvinylpyridine in which 5 to 95 mol% of the nitrogen atoms have been derived by reaction with a fatty acid halide of C8_20 and 5 to 95 mol% of the nitrogen atoms have been quaternized with HF; and 5-amino-l, 3-bis (2-ethylhexyl) -5-methylhexahydropyrimidine; wherein the barrier material is selected from the group consisting of beeswax, lanolin, sperm, carnauba wax, paraffin waxes, microcrystalline waxes, petrolatum waxes, ethylene polymer waxes, polymethylene waxes, polymethylalkysiloxane, polydimethylsiloxane, poly (perfluoroalkylmethylsiloxane), poly (methyl-3, 3, 3-tri-fluoropropylsiloxane), polytetrafluoroethylene, fluorinated polyethylene-propylene, polyvinylidene fluoride and polyvinyl fluoride; and wherein the active agent is selected from a group consisting of: 4 ', 5-dibromosalicylanilide, 3,4', 5-trichlorosalicylanilide, 3,4 ', 5-tribromosalicylanilide, 2,3,3', 5-tetrachlorosalicylanilide , 3,3,3 ', 5-tetrachlorosalicylanilide, 3,5-dibromo-3'-trifluoromethyl salicylanilide, 5-n-octanoyl-3'-trifluoromethyl salicylanilide, 3,5-dibromo-4'-trifluoromethyl salicylanilide, 3, 5-dibromo-3'-trifluoromethyl salicylanilide Methyl p-hydroxybenzoic ester P-hydroxybenzoic ethyl ester P-hydroxybenzoic propyl ester p-hydroxybenzoic butyl p-hydroxybenzoic ester 2, 4, 4'-trichloro-2-hydroxy-diphenyl ether 2 ', 2' -dihydroxy-5, 5'-dibromo-diphenyl 3,4-tricarboxylic acid, 3-trifluoromethyl-4,4'-dichlorocarbanilide, 3,3,4'-trichlorocarbanilide Phenol, 2-methyl- phenol, 3-methyl-phenol, 4-methyl-phenol, 4-ethyl-phenol, 2,4-dimethyl-phenol, 2,5-dimethyl-phenol, 3,4-dimethyl-phenol, 2,6-dimethyl- phenol, 4-n-propyl-phenol, 4-n-butyl-phenol, 4-n-amyl-phenol, 4-ter -amil-phenol, 4-n-hexyl-phenol, 4-n-heptyl-phenol, 2-methoxy-4- (2-propenyl) -phenol, 2-isopropyl-5-methyl-phenol, methyl-p-chlorophenol , ethyl-p-chlorophenol, n-propyl-p-chlorophenol, n-butyl-p-chlorophenol, n-ami1-p-chlorophenol, sec-amyl-p-chlorophenol n-hexyl-p-chlorophenol, cyclohexyl-p- chlorophenol, n-heptyl-p-chlorophenol, n-octyl-p-chlorophenol, methyl-o-chlorophenol, ethyl-o-chlorophenol, n-propyl-o-chlorophenol, n-butyl-o-chlorophenol, n-amyl- o-chlorophenol, ter-amyl-o-chlorophenol, n-hexyl-o-chlorophenol, n-heptyl-o-chlorophenol, o-benzyl-p-chlorophenol, o-benzyl-m-methyl-p-chlorophenol, or- benzyl-m, m-dimethyl-p-chlorophenol, o-phenylethi-1-p-chlorophenol, o-phenylethyl-m-methyl-1-p-chlorophenol, 3-methyl-p-chlorophenol, 3, 5-dimethyl-p-chlorophenol, 6-ethyl-3-methyl-p-chlorophenol, 6-n-propyl-3-methyl-p-chlorophenol, 6-iso-propyl-3-methyl-p-chlorophenol, 2-ethyl-3,5-dimethyl- p-chlorophenol, 6-sec-butyl-3-methyl-p-chlorophenol, 2-iso-propyl-3,5-dimethyl-p-chlorophenol, 6-diethylmethyl-3-methyl-p-chlorophenol, 6-iso-propyl-2-ethyl-3-methyl-p-chlorophenol, 2-sec-amyl-3,5-dimethyl-p-chlorophenol, 2-diethylmethyl- 3, 5-dimethyl-p-chlorophenol, 6-sec-octyl-3-methyl-p-chlorophenol, methyl-p-bromophenol, ethyl-p-bromophenol, n-propyl-p-bromophenol, n-butyl-p- bromophenol, n-amyl-p-bromophenol, sec-amyl-p-bromophenol, n-hexyl-p-bromophenol, cyclohexyl-p-bromophenol, ter-amyl-o-bromophenol, n-hexyl-o-bromophenol, n- propyl-mm-dimethyl-o-bromophenol, 2-phenylphenol, 4-chloro-2-methylphenol, 4-chloro-3-methylphenol, 4-chloro-3,5-dimethylphenol, 2,4-dichloro-3,5-dimethylphenol, 3,4,5,6-tetrabromo-2-methylphenol, 5-methyl-2-pentylphenol, 4-isopropyl-3-methylphenol, 5-chloro-2-hydroxydiphenylmethane, resorcinol, methyl-resorcinol, ethyl-resorcinol, n-propyl-resorcinol, n-butyl-resorcinol, n-amyl- resorcinol, n-hexyl-resorcinol, n-heptyl-resorcinol, n-octyl-resorcinol, n-nonyl-resorcinol, phenyl-resorcinol, benzyl-resorcinol, phenylethyl-resorcinol, phenylpropyl-resorcinol, p-chlorobenzyl-resorcinol, 5- chloro-2, -dihydroxydiphenylmethane, 4'-chloro-2,4-dihydroxydiphenylmethane, 5-bromo-2,4-dihydroxydiphenylmethane, 4'-bromo-2,4-dihydroxydiphenylmethane, 2,2'-methylene bis (4-chlorophenol ), 2,2 '-methylene bis (3,4,6-trichlorophenol), 2,2'-methylene bis (4-chloro-6-bromophenol), bis (2-hydroxy-3,5-dichlorophenyl) sulfide , bis (2-hydroxy-5-chlorobenzyl) sulfide, benzethonium chloride, diisobutylphenoxy-phenoxyethyl-ethyl-dimethyl-benzyl ammonium chloride, cetylpyridinium chloride, cetylpyridinium bromide, cetylpyridinium iodide, cetylpyridinium fluoride, dodecyltrimethylammonium bromide, benzyldimethylstearylammonium chloride, monocyclic oxazolidines, bicyclic oxazolidines, polymeric bicyclic oxazolidines, oxazalidines 1-3-dioxanes, oxazolidinones, 5-amino-l, 3-bis (2-ethylhexyl) -5-methyl hexahydropyrimidine, 1,6-bis- ( p-chlorophenyldiguanidine) hexane, 1,6-di- (2-ethylhexyldiguanidine) hexane, 1,1'-hexamethylene-bis-. { 5- (4-fluorophenyl) -diguanidine} , sodium fluoride, potassium fluoride, tin fluoride, zinc fluoride, oleylamino fluoride, cetylamino fluoride, ethanolaminohydrofluoride, potassium hexafluorosilicate, sodium hexafluorosilicate, sodium fluorophosphate, ammonium fluorophosphate, potassium fluorophosphate, magnesium fluorophosphate . calcium fluorophosphate sodium fluorozirconate, potassium fluorozirconate tin fluorozirconate penicillin, polymyxin B, vancomycin, kanamycin, erythromycin, nidamycin, metronidazole, spiramycin and tetracycline. The composition according to claim 6, characterized in that it comprises from 2 to 5% by weight, based on the total weight of (a '), (b') and (c ') of the transfer agent; from 85 to 93% by weight, based on the total weight of (a1), (b1) and (c1) of the barrier material; and 5 to 10% by weight, based on the total weight of (a1), (b ') and (c') of the active agent. 8. The composition according to claim 6, characterized in that the transfer agent is 5-amino-l, 3-bis (2-ethylhexyl) -5-methylhexa-hydropyrimidine. 9. The composition according to claim 6, characterized in that the transfer agent is polyethyleneimine in which 5 to 95% mol of the nitrogen atoms have been derived by reaction with a fatty acid halide of C8_20 and 5 to 95 % in mol of the nitrogen atoms have been quaternized with HF. 10. The composition according to claim 6, characterized in that the barrier material is a microcrystalline wax. 11. The composition according to claim 6, characterized in that the active agent is 1,6-bis- (p-chlorophenyldiguanidine) hexane. 12. A method for the protection of teeth, characterized in that it comprises treating the tooth with a composition comprising: (a) from 1 to 20% by weight, based on the total weight of (a) and (b) of a transfer agent; and (b) from 80 to 99% by weight, based on the total weight of (a) and (b) of a barrier material; wherein the transfer agent is selected from the group consisting of the compounds of the formula (I), (II) and (III): R 'R' R 'RN 1 -R "RN ± HX" RN' ± R »X "(I) (ID (III) where R is an alkyl chain of 8_2Q which can be substituted with one or more hydroxy groups, R ', R "and R"' each independently are an alkyl chain of Cg_2o »which can be substituted with one or more hydroxy groups, a C1-4 alkyl group, which may be substituted with one or more hydroxy groups, an aryl group of c6-10 ° hydrogen, and X is fluorine or bromine; laurylpyridinium chloride; laurylpyridinium bromide; cetylpyridinium chloride; cetylpyridinium bromide; fluoride, cetylpyridinium; cationic petroleum derivatives; polydimeryl polyamines; polyamides; polyacrylamides, polydiallyl dimethyl ammonium chlorides, polyhexamethylene biguanides; polymethobromide of 1,5-dimethyl-l, 5-diazaundecamethylene; polyvinyl pyrrolidones; polypeptides, poly (allylamine) hydrochloride; polyoxyethylene amines; polyethylene imines; acylated polyethylenimines; diethylaminoethyl cellulose; poly (vinyl-benzylstearylbetaine); poly (vinylbenzylmethylaurylammonium chloride) poly (vinylbenzyluril pyridylpyridinium chloride) poly (vinylbenzylcetylmonylhexylether) compound of the formula RN (CH3) [CC2HyO)? H] 2 (+) A (-) wherein A (-) is chloro or fluoro, X is a number from 1 to 20 and R is an alkyl group of Cg_22; polyacrylamide in which 5 to 95 mol% of the nitrogen atoms have been derived by reaction with a fatty acid halide of Cg_20 and 5 to 95 mol% of the nitrogen atoms have been quaternized with HF; polyvinylpyridine in which 5 to 95 mol% of the nitrogen atoms have been derived by reaction with a fatty acid halide of Cg_20 and 5 to 95 mol% of the nitrogen atoms have been quaternized with HF; and 5-amino-l, 3-bis (2-ethylhexyl) -5-methylhexahydropyrimidine; and wherein the barrier material is selected from the group consisting of beeswax, lanolin, sperm, carnauba wax, paraffin waxes, microcrystalline waxes, petrolatum ~ waxes, ethylene polymer waxes, polymethylene waxes, polymethylalkysiloxane, polydimethylsiloxane , poly (perfluoroalkylmethylsiloxane), poly (methyl-3,3,3-trifluoropropylsiloxane), polytetrafluoroethylene, fluorinated polyethylene-propylene, polyvinylidene fluoride and polyvinyl fluoride. The method according to claim 12, characterized in that it comprises 3 to 5% by weight, based on the total weight of (a) and (b) of the transfer agent; and 95 to 97% by weight, based on the total weight of (a) and (b) of a barrier material. The method according to claim 12, characterized in that the transfer agent is 5- amino-1,3-bis (2-ethylhexyl) -5-methylhexahydropyrimidine. The method according to claim 12, characterized in that the transfer agent is polyethyleneimine in which 5 to 95% mol of the nitrogen atoms have been derived by reaction with a fatty acid halide of C8_20 and 5 to 95 % in mol of the nitrogen atoms have been quaternized with HF. 16. The method according to claim 12, characterized in that the barrier material is a microcrystalline wax. 17. A method for the protection of the teeth characterized in that it comprises the treatment of the teeth with a composition comprising: (a ') from 1 to 10% by weight, based on the total weight of (ar), (b') and (c ') of a transfer agent; (b ') from 70 to 98% by weight, based on the total weight of (a1), (b') and (c ') of a barrier material; and (c ') 1 to 20% by weight, based on the total weight of (a'), (b1) and (c ') of an active agent; wherein the transfer agent is selected from the group consisting of the compounds of the formula (I), (II) and (III): R "R 'R" lll RNR "RN ± H X- RN ± R" X "( I) (II) (III) where R is an alkyl chain of C8_2Q, which can be substituted with one or more hydroxy groups, R ', R "and R"' each independently are an alkyl chain of CR_20 '^ which can be substituted with one or more hydroxy groups, an alkyl group of c1_4, which may be substituted with one or more hydroxy groups, an aryl group of c6-10 ° hydrogen, and X is fluorine or bromine; laurylpyridinium chloride; laurylpyridinium bromide; cetylpyridinium chloride; cetylpyridinium bromide; cetylpyridinium fluoride; cationic petroleum derivatives; polydimeryl polyamines; polyamides; polyacrylamides, polydiallyl dimethyl ammonium chlorides, polyhexamethylene biguanides; 1, 5-dimethyl-1, 5-diazaundecamethylene polymethobromide; polyvinyl pyrrolidones; polypeptides, poly (allylamine) hydrochloride; polyoxyethylene amines; polyethylene imines; acylated polyethylenimines; diethylaminoethyl cellulose; poly (vinyl-benzylstearylbetaine); poly (vinylbenzylmethylaurylammonium chloride; poly (vinylbenzylurilpyridylpyridinium chloride); poly (vinylbenzylcetylmonylhexylether); compound of the formula RN (CH3) [CC2HyO)? H] 2 (+) A (-), where A (-) is chloro or fluoro, X is a number from 1 to 20 and R is an alkyl group of Cg_22; polyacrylamide in which 5 to 95 mol% of the nitrogen atoms have been derived by reaction with a fatty acid halide of C8_20 and 5 to 95 mol% of the nitrogen atoms have been quaternized with HF; polyvinylpyridine in which 5 to 95 mol% of the nitrogen atoms have been derived by reaction with a fatty acid halide of Cg_20 and 5 to 95 mol% of the nitrogen atoms have been quaternized with HF; and 5-amino-l, 3-bis (2-ethylhexyl) -5-methylhexahydropyrimidine; wherein the barrier material is selected from the group consisting of beeswax, lanolin, sperm, carnauba wax, paraffin waxes, microcrystalline waxes, petrolatum waxes, ethylene polymer waxes, polymethylene waxes, polymethylalkysiloxane, polydi ethylsiloxane, poly (perfluoroalkylmethylsiloxane), poly (methyl-3, 3, 3-tri-fluoropropylsiloxane), polytetrafluoroethylene, fluorinated polyethylene-propylene, polyvinylidene fluoride and polyvinyl fluoride; and wherein the active agent is selected from a group consisting of: 4 ', 5-dibromosalicylanilide, 3,4', 5-trichlorosalicylanilide, 3,4 ', 5-tribromosalicylanilide, 2,3,3', 5-tetrachlorosalicylanilide , 3,3,3 ', 5-tetrachlorosalicylanilide, 3,5-dibromo-3' -trifluoromethyl salicylanilide, 5-n-octanoyl-3 '-trifluoromethyl salicylanilide, 3,5-dibromo-4'-trifluoromethyl salicylanilide, 3, 5-dibromo-3'-trifluoromethyl salicylanilide Methyl p-hydroxybenzoic ester P-hydroxybenzoic ethyl ester P-hydroxybenzoic propyl ester p-hydroxybenzoic butyl p-hydroxybenzoic ester 2, 4, 4'-trichloro-2-hydroxy-diphenyl ether 2 ', 2'-dihydroxy-5,5'-dibromo-diphenyl ether 3,4,4'-trichlorocarbanilide, 3-trifluoromethyl-4,4'-dichlorocarbanilide, 3,3,4'-trichlorocarbanilide

Phenol, 2-methyl-phenol, 3-methyl-phenol, 4-methyl-phenol, 4-ethyl-phenol, 2,4-dimethyl-phenol, 2,5-dimethyl-phenol, 3,4-dimethyl-phenol, 2, 6-dimethyl-phenol, 4-n-propyl-phenol, 4-n-butyl-phenol, 4-n-amyl-phenol, 4-tert-amyl-phenol, 4-n-hexyl-phenol, -n heptyl-phenol, 2-methoxy-4- (2-propenyl) -phenol, 2-isopropyl-5-methyl-phenol, methyl-p-chlorophenol, ethyl-p-chlorophenol, n-propyl-p-chlorophenol, n-butyl-p-chlorophenol, n-amyl-p-chlorophenol, sec-ami1- p-chlorophenol n-hexyl-p-chlorophenol, cyclohexyl-p-chlorophenol, n-heptyl-p-chlorophenol, n-octyl-p-chlorophenol, methyl-o-chlorophenol, ethyl-o-chlorophenol, n-propyl-o -chlorophenol, n-butyl-o-chlorophenol, n-amyl-o-chlorophenol, tert-amyl-o-chlorophenol, n-hexyl-o-chlorophenol, n-heptyl-o-chlorophenol, o-benzyl-p-chlorophenol , o-benzyl-m-methyl-p-chlorophenol, o-benzyl-m, m-dimethyl-p-chlorophenol, o-phenylethyl-p-chlorophenol, o-phenylethyl-m-methyl-p-chlorophenol, 3 - . 3-methyl-p-chlorophenol, 3,5-dimethyl-p-chlorophenol, 6-ethyl-3-methyl-p-chlorophenol, 6-n-propyl-3-methyl-p-chlorophenol, 6 -. 6-isopropyl-3-methyl-p-chlorophenol, 2 - . 2 - . 2-ethyl-3,5-dimethyl-p-chlorophenol, 6 -sec-butyl-3-methyl-p-chlorophenol, 2-isopropyl-3,5-dimethyl-p-chlorophenol, 6-diethylmethyl-3-methyl-p-chlorophenol, 6-iso-propyl-2-ethyl-3-methyl-p-chlorophenol, 2-sec-amyl-3, 5-dimethyl-p-chlorophenol,
2-diethylmethyl-3,5-dimethyl-p-chlorophenol, 6-sec-octyl-3-methyl-p-chlorophenol, methyl-p-bromophenol, ethyl-p-bromophenol, n-propyl-p-bromophenol, n-butyl-p-bromophenol, n-amyl-p-bromophenol, sec-amyl-p-bromophenol, n-hexyl-p-bromophenol, cyclohexyl-p-bromophenol, tert-amyl-o-bromophenol, n-hexyl-o-bromophenol, n-propyl-mm-dimethyl-o-bromophenol, 2-Phenylphenol, 4-chloro-2-methylphenol, 4-chloro-3-methylphenol, 4-chloro-3,5-dimethylphenol, 2,4-dichloro-3,5-dimethylphenol, 3,4,5,6- tetrabromo-2-methylphenol, 5-methyl-2-pentylphenol, 4-isopropi1-3- eti1fenol, 5-chloro-2-hydroxydiphenylmethane, resorcinol methyl-resorcinol, ethyl-resorcinol, n-propyl-resorcinol, n-butyl- resorcinol, n-amyl-resorcinol, n-hexyl resorcinol, n-heptyl-resorcinol, n-octyl-resorcinol, n-nonyl-resorcinol, phenyl-resorcinol, benzyl-resorcinol, phenylethyl-resorcinol, phenylpropyl-resorcinol, p- chlorobenzyl-resorcinol, 5-chloro-2, 4 -dihidroxidifenilmetano, 4 '-chloro-2, 4 -dihidroxidifenilmetano, 5-bromo-2, 4 -dihidroxidifenilmetano, 4'-bromo-2, 4 -dihidroxidifenilmetano, 2,2' -met ilen bis (4-chlorophenol), 2,2'-methylene bis (3,4,6-trichlorophenol), 2,2'-methylene bis (4-chloro-6-bromophenol), bis (2-hydroxy) sulfide 3, 5-dichlorophenyl) sulfide bis (2-hydroxy-5-chlorobenzyl), benzethonium chloride, diisobutylphenoxyethoxyethyl dimethyl benzyl ammonium chloride, cetylpyridinium chloride, cetylpyridinium bromide, iodide, cetylpyridinium fluoride, cetylpyridinium dodecyltrimethylammonium bromide , benzyldimethylstearylammonium chloride, monocyclic oxazolidines, bicyclic oxazolidines, bicyclic oxazolidines polymer, oxazalidinas 1-3-dioxanes, oxazolidinones, 5-amino-l, 3-bis (2-ethylhexyl) -5-methyl hexahidropiri idina, 1, 6-bis - (p-chlorophenyldiguanidine) hexane, 1,6-di- (2-ethylhexyldiguanidine) hexane, 1,1'-hexamethylene-bis-. { 5- (4-fluorophenyl) -diguanidine} , Sodium fluoride, potassium fluoride, tin fluoride, zinc fluoride, oleilamino-fluoride, cetilamino-fluoride, etanolaminohidrofluoruro, potassium hexafluorosilicate, sodium hexafluorosilicate, sodium fluorophosphate, ammonium fluorophosphate, fluorophosphate, potassium fluorophosphate, magnesium , calcium fluorophosphate fluorozirconate sodium, fluorozirconate potassium tin fluorozirconate penicillin, polymyxin B, vancomycin, kanamycin, erythromycin, nidamycin, metronidazole, spiramycin and tetracycline. The method according to claim 17, characterized in that the composition comprises from 2 to 5% by weight, based on the total weight of (a1), (b1) and (c ') of the transfer agent; from 85 to 93% by weight, based on the total weight of (a '), (b') and (C) of the barrier material; and 5 to 10% by weight, based on the total weight of (a '), (b1) and (c') of the active agent. 19. The method according to claim 17, characterized in that the transfer agent is 5-amino-1,3-bis (2-ethylhexyl) -5-methylhexahydropyrimidine. The method according to claim 17, characterized in that the transfer agent is polyethyleneimine in which 5 to 95% mol of the nitrogen atoms have been derived by reaction with a fatty acid halide of C8_20 and from 5 to 95 % in mol of the nitrogen atoms have been quaternized with HF. 21. The method according to claim 17, characterized in that the barrier material is a microcrystalline wax. 22. The method according to claim 17, characterized in that the active agent is 1,6-bis- (p-chlorophenyldiguanidine) hexane. 23. A dental delivery system, characterized in that it comprises a substrate coated with a composition comprising: (a) from 1 to 20% by weight, based on the total weight of (a) and (b) of a transfer agent; and (b) from 80 to 99% by weight, based on the total weight of (a) and (b) of a barrier material, wherein the transfer agent is selected from the group consisting of the compounds of the formula ( I), (II) and (III): R 'R « (I) (II) (III) where R represents an alkyl chain (C8_Q), which can be substituted with one or more hydroxy groups, R ', R "and R"' each independently are an alkyl chain (Cg_20), which can be substituted with one or more hydroxy groups, an alkyl 1-4) / which may be substituted with one or more hydroxy groups, an aryl group (C6_10) or hydrogen, and X is fluorine or chlorine; laurylpyridinium chloride; laurylpyridinium bromide; cetylpyridinium chloride; cetylpyridinium bromide; cetylpyridinium fluoride; cationic petroleum derivatives; polydimeryl polyamines; polyamines; polyacrylamides, polydiallyl dimethyl ammonium chlorides, polyhexamethylene biguanides; 1, 5-dimethyl, 5-diazaundecamethylene polymethobromide; polyvinyl pyrrolidones; polypeptides, poly (allylamine) hydrochloride; polyoxyethylene amines; polyethylene imines; acylated polyethylenimines; diethylaminoethyl cellulose; poly (vinyl-benzylstearylbetaine); poly (vinylbenzylmethylaurylammonium chloride) poly (vinylbenzyluril pyridylpyridinium chloride) poly (vinylbenzylcetylmonylhexylether) compound of the formula RN (CH3) [CC2HyO)? H] 2 (+) A (-) wherein A (-) is chloro or fluoro, X is a number from 1 to 20 and R is C8_22 / 'polyacrylamide alkyl in which 5 to 95 mol% of the nitrogen atoms have been derived by reaction with a halide of C8_20 fatty acid and 5 to 95 mol% of the nitrogen atoms have been quaternized with HF; polyvinylpyridine in which 5 to 95 mol% of the nitrogen atoms have been derived by reaction with a fatty acid halide of Cg_20 and 5 to 95 mol% of the nitrogen atoms have been quaternized with HF; and 5-amino-l, 3-bis (2-ethylhexyl) -5-methylhexahydropyrimidine; and wherein the barrier material is selected from the group consisting of beeswax, lanolin, sperm, carnauba wax, paraffin waxes, microcrystalline waxes, petrolatum waxes, ethylene polymer waxes, polymethylene waxes, polymethylalkysiloxane, polydimethylsiloxane, poly. { perfluoroalkylmethylsiloxane), poly (methyl-3, 3, 3-tri-fluoropropylsiloxane), polytetrafluoroethylene, fluorinated polyethylene-propylene, polyvinylidene fluoride and polyvinyl fluoride. 24. The dental delivery system according to claim 23, characterized in that it comprises a composition of 3 to 5% by weight, based on the total weight of (a) and (b) of the transfer agent; and 95 to 97% by weight, based on the total weight of (a) and (b) of a barrier material. 25. The dental delivery system according to claim 23, characterized in that the transfer agent is 5-amino-l, 3-bis (2-ethylhexyl) -5-methylhexahydro-pyrimidine. 26. The dental delivery system according to claim 23, characterized in that the transfer agent is polyethyleneimine in which 5 to 95 mol% of the nitrogen atoms have been derived by reaction with a fatty acid halide of C8_20 and 5 to 95% by mole of the nitrogen atoms have been quaternized with HF. 27. The dental delivery system according to claim 23, characterized in that the barrier material is a microcrystalline wax. 28. A dental delivery system characterized in that it comprises a substrate coated with a composition comprising: (a ') from 1 to 10% by weight, based on the total weight of (a'), (b ') and (C) ) of a transfer agent; (b ') from 70 to 98% by weight, based on the total weight of (a'), (b ') and (c1) of a barrier material; and (c1) 1 to 20% by weight, based on the total weight of (a '), (b1) and (c') of an active agent; wherein the transfer agent is selected from the group consisting of the compounds of the formula (I), (II) and (III): R 'R' R 'III RNR "RN ± HX" RN ± R "X" (I ) (II) (III) where R is an alkyl chain of C8_2Q, which can be substituted with one or more hydroxy groups, R ', R "and R"' each independently are an alkyl chain of C8-20 '^ to which ^ - Can to be substituted with one or more hydroxy groups, a C1_4 alkyl group, which may be substituted with one or more hydroxy groups, an aryl group of c6-10 ° hydrogen, and X is fluorine or bromine; laurylpyridinium chloride; laurylpyridinium bromide; cetylpyridinium chloride; cetylpyridinium bromide; cetylpyridinium fluoride; cationic petroleum derivatives; polydimeryl polyamines; polyamides; polyacrylamides, polydiallyl dimethyl ammonium chlorides, polyhexamethylene biguanides; 1, 5-dimethyl-l, 5-diazaundecamethylene polymethobromide; polyvinyl pyrrolidones; polypeptides, poly (allylamine) hydrochloride; polyoxyethylene amines; polyethylene imines; acylated polyethylenimines; diethylaminoethyl cellulose; poly (vinyl-benzylstearylbetaine); poly (vinylbenzylmethylaurylammonium chloride; poly (vinylbenzyluril pyridylpyridinium) chloride; poly (vinylbenzylcetylmonylhexylether); compound of the formula RN (CH3) [CC2HyO)? H] 2 (+) A (-) wherein A (-) is chloro or fluoro, X is a number from 1 to 20 and R is an alkyl group of 8-22 polyacrylamide in which 5 to 95 mol% of the nitrogen atoms have been derived by reaction with a fatty acid halide of Cg_2n and 5 to 95% by mol of the nitrogen atoms have been quaternized with HF; polyvinylpyridine in which 5 to 95 mol% of the nitrogen atoms have been derivatized by reaction with a fatty acid halide of C2Q and 5 to 95 mol% of the nitrogen atoms have been quaternized with HF; and 5-amino-1,3-bis (2-ethylhexyl) -5-methylhexahydropyrimidine; wherein the barrier material is selected from the group consisting of beeswax, lanolin, sperm, carnauba wax, paraffin waxes, microcrystalline waxes, petrolatum waxes, ethylene polymer waxes, polymethylene waxes, polymethylalkysiloxane, polydimethylsiloxane, poly (perfluoroalkylmethylsiloxane), poly (methyl-3,3,3-tri-fluoropropylsiloxane), polytetrafluoroethylene, fluorinated polyethylene-propylene, polyvinylidene fluoride and polyvinyl fluoride, and wherein the active agent is selected from a group consisting of: 4 ' , 5-dibromosalicylanilide, 3,4 ', 5-trichlorosalicylanilide, 3,4', 5-tribromosalicylanilide, 2,3,3 ', 5-tetrachlorosalicylanilide, 3,3,3', 5-tetrachlorosalicylanilide, 3,5-dibromo -3'-trifluoromethyl salicylanilide, 5-n-octanoyl-3'-trifluoromethyl salicylanilide, 3,5-dibromo-4'-trifluoromethyl salicylanilide, 3,5-dibromo-3'-trifluoromethyl salicylanilide Ester of methyl p-hydroxybenzoic Ester of ethyl p-hydroxybenzoic o Propyl p-hydroxybenzoic ester 2-butyl p-hydroxybenzoic ester, 4, 4'-trichloro-2-hydroxy-diphenyl ether 2 ', 2' -dihydroxy-5, 5 '-dibromo-diphenyl ether 3,4,4'-trichlorocarbanilide, 3-trifluoromethyl-4,4'-dichlorocarbanilide, 3,3,4'-trichlorocarbanilide Phenol, 2-methyl-phenol, 3-methyl-phenol, 4-methyl-phenol, 4-ethyl-phenol, 2,4-dimethyl-phenol, 2,5-dimethyl-phenol, 3, 4-dimethyl-phenol, 2,6-dimethyl-phenol, 4-n-propyl-phenol, 4-n-butyl-phenol, 4-n-amyl-phenol, 4-tert-amyl-phenol, 4- n-hexyl-phenol, 4-n-heptyl-phenol, 2-methoxy-4- (2-propenyl) -phenol, 2-isopropyl-5-methyl-phenol, methyl-p-chlorophenol, ethyl-p-chlorophenol, n-propyl-p-chlorophenol, n-butyl p-chlorophenol, n-amyl p-chlorophenol, sec-AMI1-p-chlorophenol n-hexyl-p-chlorophenol, cyclohexyl-p-chlorophenol, n-heptyl-p chlorophenol, n-octyl-p-chlorophenol, o-chlorophenol methyl, ethyl o-chlorophenol-n-propyl-o-chlorophenol, n-butyl-o-chlorophenol, n-amyl-o-chlorophenol, tert-AMI1 -o-chlorophenol, n-hexyl-o-chlorophenol, n-heptyl-o-chlorophenol, o-benzyl-p-chlorophenol, o-benzyl-m-methyl-p-chlorophenol, o-benzyl-m, m-dimethyl -p-chlorophenol, o-phenylethyl-p-chlorophenol, o-phenylethi-1-m-methyl-p-chlorophenol,
3 - . 3-yl-p-chlorophenol, 3, 5-dimethyl-p-chlorophenol, 6-ethyl-3-methyl-p-chlorophenol, 6-n-propyl-3-methyl-p-chlorophenol, 6-isopropyl -3-methyl-p-chlorophenol, 2-ethyl-3, 5-dimethyl-p-chlorophenol, 6 -sec-butyl-3-methyl-p-chlorophenol, 2-iso-propyl-3, 5-dimethyl-1-p -chlorophenol, 6-diethylmethyl-3-methyl-p-chlorophenol, 6-isopropyl-2-ethyl-3-methyl-p-chlorophenol, 2-sec-amyl-3,5-dimethyl-p-chlorophenol, 2-diethylmethyl-3,5-dimethyl-p-chlorophenol, 6 -. 6-sec-octyl-3-methyl-p-chlorophenol, methyl-p-bromophenol, ethyl-p-bromophenol, n-propyl-p-bromophenol, n-butyl-p-bromophenol, n-amyl-p-bromophenol, sec-amyl-p-bromophenol, n-hexyl-p-bromophenol, cyclohexyl-p-bromophenol, tert-amyl-o-bromophenol, n-hexyl-o-bromophenol, n-propyl-mm-dimethyl-o-bromophenol, 2-phenylphenol, 4-chloro-2-methylphenol, 4-chloro-3-methylphenol, 4-chloro-3,5-dimethylphenol, 2,4-dichloro-3,5-dimethylphenol, 3,4,5,6- tetrabromo-2-methylphenol, 5-methyl-2-pentylphenol, 4-isopropyl-3-methylphenol, 5-chloro-2-hydroxydiphenylmethane, resorcinol methyl-resorcinol, ethyl-resorcinol, n-propyl-resorcinol, n-butyl- resorcinol, n-amyl-resorcinol, n-hexyl resorcinol, n-heptyl-resorcinol, n-octyl-resorcinol, n-nonyl-resorcinol, phenyl-resorcinol, benzyl-resorcinol, phenylethyl-resorcinol, phenylpropyl-resorcinol, p- chlorobenzyl-resorcinol, 5-chloro-2,4-dihydroxydiphenylmethane,
4'-chloro-2, -dihydroxydiphenylmethane,
5-bromo-2,4-dihydroxydiphenylmethane, 4'-bromo-2,4-dihydroxydiphenylmethane, 2,2'-methylene bis (4-chlorophenol), 2,2'-methylene bis (3,4,
6-trichlorophenol), 2,2 '-methylene bis (4-chloro-6-bromophenol), sulfur bis (2-hydroxy-3, 5-dichlorophenyl) sulfide bis (2-hydroxy-5-chlorobenzyl), benzethonium chloride, diisobutylphenoxyethoxyethyl dimethyl benzyl ammonium chloride, cetylpyridinium chloride, cetylpyridinium bromide, iodide, cetylpyridinium fluoride cetylpyridinium, dodecyltrimethylammonium bromide, benzyldimethylstearylammonium chloride, monocyclic oxazolidines, bicyclic oxazolidines, polymeric bicyclic oxazolidines, oxazalidines 1-3-dioxanes, oxazolidinones, 5-amino-1,3-bis (2-ethylhexyl) -5-methyl hexahydropyrimidine, , 6-bis- (p-chlorophenyldiguanidine) hexane, 1,6-di- (2-ethylhexyldiguanidine) hexane, 1,1'-hexamethylene-bis-. { 5- (4-fluorophenyl) -diguanidine} , sodium fluoride, potassium fluoride, tin fluoride, zinc fluoride, oleylamino fluoride, cetylamino fluoride, ethanolaminohydrofluoride, potassium hexafluorosilicate, sodium hexafluorosilicate, sodium fluorophosphate, ammonium fluorophosphate, potassium fluorophosphate, magnesium fluorophosphate . calcium fluorophosphate sodium fluorozirconate, potassium fluorozirconate fluorozirconate of tin penicillin, polymyxin B, vancomycin, kanamycin, erythromycin, niddamycin, metronidazole, spiramycin and tetracycline. 29. The dental delivery system according to claim 28, characterized in that the composition comprises from 2 to 5% by weight, based on the total weight of (a '), (b1) and (c') of the transfer; from 85 to 93% by weight, based on the total weight of (a '), (b1) and (c1) of the barrier material; and 5 to 10% by weight, based on the total weight of (a '), (b') and (c ') of the active agent. 30. The dental delivery system according to claim 28, characterized in that the transfer agent is 5-amino-l, 3-bis (2-ethylhexyl) -5-methylhexa-hydropyrimidine. 31. The dental delivery system according to claim 28, characterized in that the transfer agent is polyethyleneimine in which 5 to 95% mol of the nitrogen atoms have been derived by reaction with a fatty acid halide of Cg_2Q and 5 to 95 mol% of the nitrogen atoms have been quaternized with HF. 32. The dental delivery system according to claim 28, characterized in that the barrier material is a microcrystalline wax. 33. The dental delivery system according to claim 28, characterized in that the active agent is 1,6-bis- (p-chlorophenyldiguanidine) hexane.