CH633178A5 - Dental sealing material in the form of a two-component system - Google Patents

Description

The invention relates to a dental sealing material in the form of a two-component system.

Polymerizable denture material is known in the prior art. It is e.g. For example, see U.S. Patents 3,066,112 (Bowen), 3,539,533 (Lee et al.) And 3,835,090 (Gander et al.), Which are hereby incorporated by reference. Such dental filling material generally contains at least one liquid polymerizable acrylate or methacrylate monomer, a diacyl peroxide polymerization catalyst or initiator and an amine accelerator to generate free radicals after reaction with the catalyst to polymerize the monomer. The material may also contain an inorganic filler and stabilizers to prevent premature polymerization.

A polymerizable dental filling material must have three properties in order to be useful for the dental technician or dentist. First, the mass should remain fluid long enough for the dental technician or dentist to mix and insert the material; this time is called "working time". Second, it should set quickly to a hard state after being inserted into the holes or fissures; the time from mixing to setting is called the «setting time». Third, the set material should harden as close as possible to its exposed surface; this hardening near the surface is called "surface hardening".

A dental filling material should therefore be put together in such a way that it has a setting time that is as short as possible, which coincides with its application time, and that the surface hardening is as complete as possible. A dental filling material is obviously of little use if it begins to harden considerably before the dentist can place it in the desired location. The setting time should be short to avoid accidental contact and contamination with oral fluid or material damage 40 before its final setting, but also for convenience for the patient and the dental technician or dentist. Finally, the quality of the surface hardening determines how close the firmly polymerized binder extends to the surface of the filling. When using the filling of fissures, the degree of surface hardening is extremely important, since there is only a thin layer of the filling material in the fissure.

Peroxide-catalyzed polymerizable dental filler material is generally prepared for storage and distribution before use in two separate masses, one containing the catalyst and no accelerator and the other containing the accelerator and no catalyst. Of these two masses, both can be liquid, both 55 pasty, one liquid and the other pasty, one liquid and the other solid, etc.

Each mass usually contains a liquid polymerizable monomer ("the binder" or "the binder") as the main component. Liquid, polymerizable Monome-60 re according to the prior art are described in the aforementioned US Pat. Nos. 3,066,112, 3,539,533 and 3,835,090.

The first mass (the "catalyst mass") contains, in addition to the binder, an appropriate amount of a peroxide polymerization catalyst, typically a diacyl per-65 oxide, e.g. in US Pat. Nos. 3,256,254 (Reinhardt) and 3,580,955 (Bafford), the latter document describing processes for their preparation and a summary list therefor.

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The second mass (the "accelerator mass" or "universal mass") contains, in addition to the binder, a suitable amount of an amine as an accelerator for the catalyst, usually substituted anilines. Some prior art accelerators are described in US Pat. Nos. 3,539,533 and 3,541,068 (Taylor) and 3,799,985 (Erickson). These anilines are generally N, N-bis (2-hydroxyethyl) substituted as described in said U.S. Patent 3,541,068 to produce improved color stability. U.S. Patent 3,799,985 discloses the accelerator N, N-bis (2-hydroxyethyl) -3,4-dimethyl-aniline.

Both compositions can also contain stabilizers to prevent their premature polymerization and to set the setting time to the desired length.

Although prior art polymerizable denture material has been successful in filling heavily filled cavities, attempts to use it to seal holes and fissures have encountered difficulties. Fissure sealants are used on healthy teeth to prevent tooth decay (tooth decay). By filling and sealing defects and fissures where caries can begin, a significant reduction in caries is achieved. In order to achieve this purpose, however, the crack-filling and fissure-sealing materials must remain firmly in the tooth for a long time, preferably longer than three years. Without such long-term adhesion, a crack-filling compound is of little value because it cannot prevent tooth decay where it does not stick. Even remaining 50% means that half of the treated teeth are unprotected against tooth decay. The term "adherent" means complete adhesion after one year in at least 90% and preferably in at least 95% of the treated first molars. Adhesion to the first molars is taken as a critical measure because they are the point of least adhesion and therefore give the most meaningful test. State-of-the-art fissure-sealing compositions did not have this permanent long-term liability and therefore, despite the great expenditure of time and money, have had only limited success.

As early as 1967, Buonocore (Journal of American Dentistry Association, July 1967, volume 75, 121-128) proposed the use of methyl a-cyanoacrylate in dental filling material for holes and fissures. In US Pat. Nos. 3,839,065 (Over-hults) and 3,663,501 (Adams), cyanoacrylate compositions are described and claimed as means for filling and sealing holes and fissures. For many years, efforts have been made to develop a cyanoacrylate composition for sealing holes and fissures, but the adhesion of these compositions is poor. The clinical study by L. Ripa and W. Cole (J. Dental Research, 49, 171 (1970) is exemplary for the study of the effect of cyanoacrylate compositions for sealing holes and fissures. Only 36.2% of the first molars had after one year the mass is still complete.

Attempts to use the binder systems of known, heavily filled dental restorative material to seal and fill holes and fissures have also had little success. Many agents of this type have not even been developed commercially because of their low liability. Even the commercial masses do not remain attached. For example, a commercial mass for sealing fissures and holes, sold by Lee Pharmaceutical Co. under the name “Epoxylite 9075”, a peroxide-catalyzed material that contains diethylene glycol dimethacrylate as a polymerizable monomer.

According to the Lee method, the accelerator mass and the catalyst mass are applied separately to an etched tooth that has previously been treated with a basic silane solution. W.P. Rock (Brit. Dent. J., 317 [1974]) showed

that after two years, the material applied by this method only adhered to 51.5% of the treated teeth (most of which were first molars). None of the first six molars remained sealed after two years in this study.

Some success has been achieved with the crack sealant, which the L.D. Caulk Company is marketed under the name «NUVA SEAL». This material, which contains about 75% by weight of BIS-GMA and about 25% by weight of methyl methacrylate, is polymerized instead of by a peroxide catalyst by irradiation with ultraviolet (UV) light. This UV irradiation process requires complex equipment and careful precautionary measures must be taken when using it for the safety of the patient and the caregiver. NUVA SEAL's liability emerged in the investigation in Kalispel, Montana, about which McCune et al. in JADA, 87, 1177 (1973) report that less than desired, the remaining on the first molars after one year being 71.8%, after two years 47.6% and after four years 11.6%. The efficacy in percent (caries reduction due to treatment, in percent) of NUVA SEAL was 80.3% after one year, 65.0% after two years and 30.5% after four years for the first molars.

None of these prior art hole and fissure sealants contain an inorganic filler. Filled materials are generally undesirable as a sealant for holes and fissures because, in contrast to unfilled materials, they have to be ground in order to restore the occlusion or closure.

In the above discussion of the known crack-sealing compositions, values for the adhesion to the first molars were given, if possible, since the first molar represents the area with the lowest adhesiveness and therefore represents the most meaningful place for the evaluation and comparison of masses.

Even NUVA SEAL, the best known mass, did not result in the sealant remaining firmly attached, as less than 50% of the treated first molars were still completely sealed after two years. It can be seen from this that no known compound for filling cracks and no method for dental treatment (and in particular no peroxide-catalyzed compound for filling fissures) resulted in long-term adhesion. There has therefore long been a need for treatment of teeth and for a mass for sealing holes and fissures that remain firmly on the teeth for a long time.

The dental sealing material according to the invention in the form of a two-component system, the two components which, after mixing, give a mixed mass for sealing tooth holes and fissures, are characterized by a) a catalyst component which comprises 40 to 60 parts by weight of a mixture of 2 , 2-bis- [4- (3-methacryloxy-2-hydroxypropyl) phenyl] propane and 0 to 3 parts by weight bis-phenol-A-dimethacrylate for each 9 parts by weight 2.2- Bis- [4- (3-meth-acryloxy-2-hydroxypropyl) phenyl] propane, 60 to 40 parts by weight of triethylene glycol dimethacrylate and a peroxide catalyst, with the catalyst component essentially no accelerator contains for the peroxide catalyst, and

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b) an accelerator component containing 40 to

60 parts by weight of a mixture of 2,2-bis- [4- (3-methacryloxy-2-hydroxypropyl) phenyl] propane and 0 to 3 parts by weight of bis-phenol-A-dimethacrylate for each 9 parts by weight of 2,2-bis- [4- (3-methacryloxy-2-hydroxypropyl) phenyl] propane, 60 to 40 parts by weight of triethylene glycol dimethacrylate and any accelerator for the Peroxide catalyst, the accelerator component being essentially free of peroxides,

c) wherein the amounts of catalyst and accelerator are such that the setting time for the mixed mass is 40 to 90 seconds, the entire catalyst and the entire accelerator are dissolved in their respective components and the mixed mass obtained has a contact angle with a dry etched Tooth surface of less than 10 ° and a Brookfield viscosity of up to 1200 cP.

It has surprisingly been found that the dental sealing material gives a firmly adhering and long-lasting protective film on the tooth surface.

A method of treating teeth to prevent tooth decay preferably includes the following steps:

1. Removal of a surface film by cleaning the tooth to be treated if necessary;

2. Etch the tooth surface with an etching solution as described below;

3. Cleaning the etched tooth surface to remove etching solution and residues;

4. drying the etched tooth surface;

5. Coating the dried, etched tooth surface with a hard, firmly adhering polymer layer by applying a drop of a liquid polymerizable monomer material, which contains a peroxide catalyst for the material and an accelerator for the catalyst dissolved, on the dry, etched tooth surface, wherein the liquid polymerizable monomeric material is a liquid polymerizable methacrylate monomer and the liquid polymerizable monomeric material forms a contact angle of less than 10 ° with the dry etched tooth surface and has a Brookfield viscosity of up to 1200 cP, the liquid polymerizable monomeric material being over the tooth surface flows and

6. Keep the tooth surface dry until the monomeric material is polymerized into a hard, firmly adhering protective layer.

A surface film or a skin-like coating is deposited on the teeth, which is usually removed at regular intervals together with the plaque. If the tooth to be treated has this surface film or coating, it is preferably removed by known cleaning methods before the etching. In some cases, however, the etching itself can clean the tooth surface sufficiently.

A suitable etching solution for use in the above-mentioned method is 35% aqueous phosphoric acid, 50% aqueous phosphoric acid etc. These etching solutions are preferred, but any solutions which effectively etch the teeth can be used.

The etched tooth surface is preferably cleaned by rinsing the mouth with water, but other cleaning methods such as wiping or wiping etc. can also be used.

It is believed - although the invention is not bound by this theory - that the good wetting and viscosity properties of the monomeric material used according to the invention are largely responsible for its adherence to the teeth. The successfully used materials have a contact angle of less than 10 ° compared to the dried, etched tooth surface, measured at 25 ° C and ambient humidity with a Rame-Hart NRL goniometer, and a Brookfield viscosity of up to 1200 cP, measured at 25 ° C and with a spindle No. 2 at 100 rpm. The compositions used preferably have a contact angle of less than 5 °, measured as indicated above, immediately after application to the dry etched tooth surface. The actual contact angle of these preferred masses is believed to be very close to 0 °, but contact angles below 5 ° are not easy to measure.

It is further assumed that the setting time of the mixed compositions according to the invention should preferably be in the range from about 40 to about 90 seconds in order to give firm adhesion to the teeth.

The monomeric material can be applied to the tooth surface with a dropper, glass rod, brush, or any other suitable device.

A preferred mixed mass for sealing holes and fissures is a peroxide catalyzed mass containing BIS-GMA, triethylene glycol dimethacrylate (TEGDM), a peroxide catalyst and an accelerator for the catalyst. This compound has good surface hardening and solid long-term hardening on the tooth.

The monomer BIS-GMA is the glycidyl methacrylate derivative of bisphenol-A, more precisely: 2,2-bis- [4- (3-methacryloxy-oxy-2-hydroxypropyl) phenyl] propane.

The composition can also contain the monomer bisphenol-A-di-methacrylate (BADM), up to 3 parts by weight of BADM per 9 parts by weight of BIS-GMA and in particular about 1 part by weight of BADM per 9 parts by weight. Parts BIS-GMA included.

The mixed compositions for sealing holes and fissures according to the invention have a setting time of 40 to 90 seconds. The types and amounts of peroxide catalyst, amine accelerator and stabilizer (if present) must be selected so that a setting time in the desired range is obtained. It is known in the denture art that the setting time can be reduced by adding stabilizers. It should be noted that double to three times the preferred amount of peroxide catalyst and amine accelerator can be used up to the respective solubility limit of polymerizable monomer. If a large amount of one of these two agents is used, the amount of the other can be correspondingly small in order to keep the setting time in the desired range. When stabilizers are added, the amounts of accelerator and catalyst can be increased to keep the setting time in the desired range.

Any prior art accelerator is used as long as the setting time of the mass obtained is in the desired range. Preferred accelerators are N, N-bis (2-hydroxyethyl) -4-methylaniline and N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline, in particular N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline used.

The preferred peroxide catalyst for the dental sealing material according to the invention is benzoyl peroxide, but other peroxide catalysts can be used as long as the setting time of the mass is in the desired range. Since the compositions according to the invention are peroxide-catalyzed, the disadvantages of UV catalysis are avoided.

Stabilizers can also be added to the material to prevent its premature polymerization during storage or to set the setting time. Such stabilizers are generally compounds that terminate free radical chain reactions, e.g.

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a substituted phenol, e.g. B. p-methoxyphenol, 2,5-di-t-butyl-4-methylphenol (called BHT), a compound of the formula:

0

H

ICH2OC-CH2CH2

(sold by Geigy Chemical Company under the name Irganox 1010) etc.

A particularly preferred dental sealing material according to the invention contains from about 40 to about 60 parts by weight of BIS-GMA, about 60 to about 40 parts by weight of TEDGM, about 1.0 to about 3.0 parts by weight of N, N-bis- (2-hydroxyethyl) -4-methylaniline and about 0.5 to about 1.5 parts by weight of benzoyl peroxide. A particularly preferred material of this type contains about 40 to about 60 parts by weight of a mixture of 9 parts by weight of BIS-GMA and up to about 3, preferably about 1 part by weight of BADM, about 60 to about 40 parts by weight. Parts of TEGDM, about 1.0 to about 3.0 parts by weight of N, N-bis (2-hydroxyethyl) -4-methylaniline and about 0.5 to about 1.5 parts by weight of benzoyl peroxide.

The most preferred dental sealing material according to the invention contains all of the materials mentioned in one of the above compositions, but with about 0.6 to about 1.8 parts by weight of N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline instead of the N, N-bis (2-hydroxyethyl) -4-methylaniline used above occurs.

It should be emphasized that the above-mentioned masses are produced and exist as two separate masses, one containing the catalyst and no accelerator and the other containing the accelerator and no catalyst. Each of these compositions preferably contains the same amount of polymerizable monomer and differs only in the presence of peroxide or amine accelerator and the amount of stabilizer. These two masses are then combined to seal holes and fissures, which mass is then applied to the tooth.

The present invention is further illustrated by the following examples. All parts are parts by weight unless otherwise stated.

Example I

Mixing the following ingredients produces two masses:

90:10 BIS-GMA: BADM TEGDM

BHT (stabilizer) benzoyl peroxide

N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline

45.00 55.00 0.05

2.40

B

45.00 55.00 0.15 2.00

If equal parts by weight of mass A and mass B are mixed together and applied to a dry etched tooth, the material applied shows good surface strength and firm adhesion to the tooth.

Example II

Two corresponding compositions are prepared according to the process of Example I, but in the composition A 4.00 parts of N, N-bis (2-hydroxyethyl) -4-methylaniline instead of the N, N-bis (2-hydroxyethyl) Use 3,4-dimethylaniline and 0.04 part BHT instead of the 0.05 part used. The set material produced by mixing equal parts by weight of the two masses has good surface hardening and firm adhesion to the tooth, as described in experiment 2.

Trial 1

An investigation (0766-01-19) of the adhesion of the mass io according to Example I and its effectiveness in preventing tooth decay was carried out on 200 six- to seven-year-old children. Each child had at least one pair of healthy first molars, with one molar from each pair statistically selected for treatment and the other one used as a comparison.

The following procedure was used in this investigation:

1) All teeth were cleaned by brushing with toothpaste.

20 2) The teeth were checked twice to see if there was a caries-free pair of corresponding first molars. These two independent exams had to match for the child to be included in the exam.

25 3) The tooth to be treated was determined using a statistical number table.

4) The tooth to be treated was prepared by etching with a 35% aqueous phosphoric acid and rinsing with water, and was then dried and washed with cotton wool.

30 rolls blocked.

5) The sealant was applied as a drop, run over the tooth surface and allowed to set.

The condition of the 304 pairs of teeth (304 treated and 304 35 comparison teeth) six months after treatment is shown in the following table.

Table I

Condition of the pairs of treated teeth and 40 comparison teeth after six months

Upper

Lower

Together

teeth

Teeth men

45 Both teeth healthy

138

94

232

Both teeth carious

1

0

1

Treated tooth healthy,

Comparative tooth carious

32

38

70

Treated tooth carious,

so comparison tooth healthy

0

1

1

Adjusted benefit

32

37

69

Percent effectiveness

-

-

97.2%

55 The table shows that the effectiveness of the material according to the invention in the prevention of caries is 97.2% (adjusted projection divided by the number of carious comparison teeth). Of the 304 teeth treated, 296 (97.4%) retained the sealant 6o completely. Of the 8 teeth that lost the sealant, none lost it completely. 7 were upper teeth.

Trial 2

A comparative study (0766-01-18) for the remaining 65 of the mass according to Example II and NUVA SEAL was carried out on 385 children of seven years or less according to the procedure in Experiment 1, but with NUVA SEAL brushed onto the tooth surface

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has been. Each child had at least one pair of healthy homologous first molars, one tooth from each pair was statistically selected for treatment with either NUVA SEAL or the mass according to Example II and the other was used as a comparison. The following tables show the results one year after treatment in the examination of 300 children (145 with NUVA SEAL, 155 with the mass according to Example II) and 576 tooth pairs (237 with NUVA SEAL, 239 with the mass according to Example II).

Table II Adhesion of the sealant

Complete partial stay no stay

B

NUVA SEAL mass according to Example II

83.5% 94.6%

10.6% 2.5%

5.9% 2.9%

Table purple condition of the pairs NUVA SEAL-treated comparison

Upper

Lower

Together

teeth

Teeth men

Both teeth healthy

93

108

201

Both teeth carious

1

1

2nd

Treated tooth healthy,

Comparative tooth carious

22

8th

30th

Treated tooth carious,

Comparison tooth healthy

1

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Pure advantage

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5

26

Percent effectiveness

91.3

55.6

81.2

Table IHb Condition of the pairs treated with mass according to Example II and comparison teeth

Upper

Lower

Together

teeth

Teeth men

Both teeth healthy

90

103

193

Both teeth carious

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4th

7

Treated tooth healthy,

Comparative tooth carious

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14

39

Treated tooth carious,

Comparison tooth healthy

0

0

0

Pure advantage

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39

Percent effectiveness

89.3

77.8

84.8

BIS-GMA 40.00 40.00

TEGDM 60.00 60.00

5 BHT (stabilizer) * *

Benzoyl peroxide 2.00 N, N-bis- (2-hydroxyethyl) -3,4-di-

methylaniline 2.40

10 * stabilizer quantities for a setting time of 40 to 90 seconds

If the same parts by weight of masses A and B are mixed together and applied to a dry etched tooth, the set material has good surface hardness and adheres firmly to the tooth.

Example IV

According to the process according to Example III, two corresponding masses were produced, but 4.00 parts of 20 N, N-bis (2-hydroxyethyl) -4-methylaniline and the N, N-bis (2-hydroxyethyl) -3 used therein , Replace 4-dimethylaniline. The set material produced by mixing equal parts by weight of the two masses has good surface hardness and adheres firmly to the tooth.

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Example V

Mixing the following ingredients produces two masses:

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B

60.00 40.00

2.40

60.00

40.00 *

2.00

BIS-GMA TEGDM

BHT (stabilizer)

35 benzoyl peroxide N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline

* Stabilizer quantities for a setting time of 40 to 90 seconds

40 If the same parts by weight of materials A and B are mixed together and applied to a dry etched tooth, the set material has good surface hardening and adheres firmly to the tooth.

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Example VI

Two corresponding compositions were prepared in accordance with the process according to Example V, but instead of the N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline used, 5 (J4.00 parts of N, N-bis- (2- hydroxyethyl) -4-methylaniline were used, the hardened material produced by mixing equal parts by weight of the two masses has good surface hardening and adheres firmly to the tooth.

From the tables above it can be seen that the masses according to Example II remained more than 11% more completely on the tooth than NUVA SEAL and had a higher percentage of effectiveness, especially in the lower teeth. It should be emphasized that there is a significant relationship between complete retention and prevention of caries in the long term, which is not clearly shown by this study due to the short period examined.

Example III

Two masses were made by mixing the following ingredients:

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Example VII

Mixing the following ingredients produces two masses:

60

B

65

90:10 BIS-GMA: BADM 40.00 40.00

TEGDM 60.00 60.00

BHT (stabilizer) * *

Benzoyl peroxide 2.00 N, N-bis- (2-hydroxyethyl) -3,4-di-

methylaniline 2.40

* Stabilizer quantities for a setting time of 40 to 90 seconds

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If equal amounts of mass A and B are mixed together and applied to a dry etched tooth, the set material has good surface hardening and adheres firmly to the tooth.

Example VIII

Two corresponding compositions were prepared in accordance with the process according to Example VII, but the N, N-bis- (2-hydroxyethyl) -3,4-dimethylaniline used therein was made up by 4.00 parts of N, N-bis- (2-hydroxyethyl) -4-methylaniline was replaced. The set material produced by mixing equal parts by weight of the two masses has good surface hardening and adheres firmly to the tooth.

Example IX

Mixing the following ingredients produces two masses:

B

60.00

40.00 *

90:10 BIS-GMA: BADM TEGDM

BHT (stabilizer)

Benzoyl peroxide N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline 2.40

* Stabilizer quantities for a setting time of 40 to 90 seconds

60.00

40.00 *

2.00

Example XII

According to the process according to Example XI, two corresponding masses are prepared, but 2.50 parts of N, N-bis- (2nd.) Instead of the N, N-bis (2-hydroxyethyl) -3,4-dimethyl-5 aniline used there -hydroxyethyl) -4-methylaniline can be used. The set material produced by mixing equal parts by weight of the two masses has good surface hardening and adheres firmly to the tooth.

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Example XIII

Mixing the following ingredients produces two masses:

B

1.00

90:10 BIS-GMA: BADM 45.00 45.00

TEGDM 55.00 55.00

BHT (stabilizer) * 20 benzoyl peroxide N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline 3.20

* Stabilizer quantities for a setting time of 40 to 90 seconds

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If the same parts by weight of materials A and B are mixed together and applied to a dry etched tooth, the set material has good surface hardening and adheres firmly to the 30 tooth.

If the same parts by weight of materials A and B are mixed together and applied to a dry etched tooth, the set material has good surface hardening and adheres firmly to the tooth.

Example X

According to the method of Example IX, two corresponding masses are produced, but 4.00 parts of N, N-bis (2-hydroxyethyl) -4-methylaniline instead of the N, N-bis (2-hydroxyethyl) -3 used therein , 4-dimethylaniline can be used. The set material produced by mixing equal parts by weight of the two masses has good surface hardening and adheres firmly to the tooth.

Example XI

Mixing the following ingredients produces two masses:

90:10 BIS-GMA: BADM TEGDM

BHT (stabilizer) benzoyl peroxide

N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline

45.00

55.00 *

1.40

B

45.00

55.00 *

3.00

* Stabilizer quantities for a setting time of 40 to 90 seconds

If equal parts of masses A and B are mixed together and applied to a dry etched tooth, the set material has good surface hardening and adheres firmly to the tooth.

Example XIV

According to the method of Example XIII, two corresponding masses are produced, but the N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline used therein by 6.00 parts of N, N-bis (2-hydroxyethyl) ) -4-methylaniline is replaced. The set material produced by mixing equal parts by weight of the two materials has good surface hardening and adheres firmly to the 40 tooth.

Example XV

Two 45 masses are made by mixing the following ingredients:

90:10 BIS-GMA: BADM 50 TEGDM BHT (stabilizer) benzoyl peroxide

N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline

45.00 55.00

3.20

B

45.00

55.00 *

3.00

* Stabilizer quantities for a setting time of 40 to 90 seconds

If the same parts by weight of materials A and B are mixed together and applied to a dry etched 60 tooth, the set material has good surface hardening and adheres firmly to the tooth.

Example XVI

65 According to the procedure of Example XV, two corresponding masses are produced, but the N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline used is replaced by 6.00 parts of N, N-bis (2-hydroxyethyl) -4-methylaniline replaced

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becomes. The set material produced by mixing equal parts by weight of the two masses has good surface hardening and adheres firmly to the tooth.

Example XVII

Mixing the following ingredients produces two masses:

A B

90:10 BIS-GMA: BADM 45.00 45.00

TEGDM 55.00 55.00

BHT (stabilizer) * *

Benzoyl peroxide 1.00 N, N-bis (2-hydroxyethyl) -3,4-di-

methylaniline 1.40

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If the same parts by weight of materials A and B are mixed together and applied to a dry etched tooth, the set material has good surface hardening and adheres firmly to the 5 tooth.

Example XVIII Two corresponding compositions are prepared in accordance with the process according to Example XVII, but using the N, N-bis- (2-hydroxyethyl) -3,4-dimethylanioline used with 2.50 parts of N, N-bis- (2 -hydroxyethyl) -4-methylaniline replaced. The material produced by mixing equal parts by weight of the two masses has good surface hardening and adheres firmly to the tooth.

* Stabilizer quantities for a setting time of 40 to 90 seconds

Claims (6)

633 178 PATENT CLAIMS 1. Dental sealing material in the form of a two-component system, the two components, after mixing, giving a mixed mass for sealing tooth holes and fissures, characterized by a) a catalyst component which comprises 40 to 60 parts by weight of a mixture of 2.2 Bis- [4- (3-methacryloxy-2-hydroxypropyl) phenyl] propane and 0 to 3 parts by weight bis-phenol-A-dimethacrylate for each 9 parts by weight 2,2-bis- [ 4- (3-meth-acryloxy-2-hydroxypropyl) phenyl] propane, 60 to 40 parts by weight of triethylene glycol dimethacrylate, and a peroxide catalyst, the catalyst component containing essentially no accelerator for the peroxide catalyst, and b) an accelerator component containing 40 to 60 parts by weight of a mixture of 2,2-bis- [4- (3-meth-acryloxy-2-hydroxypropyl) phenyl] propane and 0 to 3 parts by weight of bis-phenol-A-dimethacrylate per 9 parts by weight of 2,2-bis- [4- (3-methacryloxy-2-hydroxypropyl) phenyl] propane, 60 to 40 parts by weight. Parts of triethylene glycol dimethacrylate, and any accelerator for the peroxide catalyst, the accelerator component being essentially free of peroxides, c) wherein the amounts of catalyst and accelerator are such that the setting time for the mixed mass is 40 to 90 seconds, the entire catalyst and the entire accelerator are dissolved in their respective components and the mixed mass obtained has a contact angle with a dry etched Tooth surface of less than 10 ° and a Brookfield viscosity of up to 1200 cP. 2. Dental sealing material according to claim 1, characterized in that in the accelerator component b) the accelerator for the peroxide catalyst N, N-bis (2-hydroxyethyl) -3,4-dimethylaniline or N, N-bis- (2- 5 hydroxyethyl) -4-methylaniline. 3. Dental sealing material according to claim 1, characterized in that the peroxide catalyst is benzoyl peroxide. 4. Dental sealing material according to the 10 Claims 1 to 3, characterized in that the benzoyl peroxide in an amount of 1.0 to 3.0 parts by weight, based on the weight of the catalyst component, and the N, N-bis (2-hydroxyethyl) -3 , 4-dimethylaniline in an amount of 1.2 to 3.6 parts by weight, based on the 15 importance of the accelerator component. 5. Dental sealing material according to one of claims 1 to 4, characterized in that it contains one part by weight of bis-phenol-A-dimethacrylate per 9 parts by weight. Contains 20 parts of 2,2-bis- [4- (3-methacryloxy-2-hydroxypropyl) phenyl] propane. 6. Dental sealing material according to claim 5, characterized in that the peroxide catalyst is benzoyl peroxide. 25 7. Dental sealing material according to claim 6, characterized in that the benzoyl peroxide in an amount of 1.0 to 3.0 parts by weight, based on the weight of the catalyst component, and the N, N-bis- (2-hy- droxyethyl) -3,4-dimethylaniline in an amount of 1.2 to 30 3.6 parts by weight, based on the weight of the accelerator component, are present.