Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K6/00—Preparations for dentistry
  • A61K6/90—Compositions for taking dental impressions

Definitions

• the invention relates to preparations based on aziridino polyethers and their use for the production of dental materials, in particular impression materials.
• DE-C-174 58 10 describes the production of moldings based on aziridinopolyethers.
• compositions based on aziridino polyethers are notable for their hydrophilic character, which enables a very high precision of the impressions.
• a disadvantage of these materials is that they cannot be removed from the mold too easily. This means that the demoldability of the impression when taking the impression and the demouldability of the plaster model after the impression is poured out are unsatisfactory.
• DE-A-197 40 234 describes dental compositions based on polyether derivatives which are characterized in that their content of cyclic oligomeric polyethers is less than 5.0%. It is described that the cyclic polyether oligomers present in the polyether compositions are responsible for the poor demouldability of the impression when taking the impression and a poor demoldability of the plaster model after pouring the impression.
• the object of the present invention is to provide dental compositions based on aziridino polyethers which are characterized by easier demoldability.
• dental compositions based on polyether preferably have Shore A hardnesses in the range from 45 to 55.
• the dental compositions formulated from the preparations according to the invention comprise in particular two components, namely the catalyst component and the base component.
• the catalyst component contains at least one starter substance and the base component contains the azine dinopolyethers.
• the individual active ingredients or groups of active ingredients which are suitable for achieving good processability and for achieving the desired combination of properties of the cured elastomers can be present in proportion in the catalyst component and the base component or in only one of the components.
• the distribution of these active ingredients among the components depends on the desired mixing ratio, the ease of mixing and the sufficient shelf life of the resulting substance mixtures in the separately stored components.
• This division can be optimized by appropriate test series.
• the properties that can be achieved during the taking of the impression and in the hardened impression material depend largely on the mixing quality and the overall composition of the impression preparation.
• a sufficient level of mixing is achieved with manual mixing, for example, by intensive spatulas on a mixing block until the mixture is colored uniformly from the differently colored components. It is advantageous to carry out the mixing in practice by means of continuous mixers, usually consisting of a volume metering unit and static or dynamic mixing elements.
• the volume mixing ratio between the catalyst component and the base component is usually set to values from 1: 1 to 1:10, the settings 1: 2 and 1: 5 being particularly preferred.
• compositions according to the invention based on polyether with improved mold release properties and improved flow behavior are obtained from preparations containing:
• the weight ratio between the components (A) and (C) to the compounds of component (B) is 1.2 to 2.1, preferably 1.3 to 1.9, • component (B) from compounds with molar masses smaller 500 g / mol (B1) and from trisacyl esters of glycerol of non-animal origin Molar masses between 500 to 2000 g / mol (B2) and compounds with molar masses greater than 2000 g / mol (B3) and
• the aziridino polyethers used in accordance with component (A) can be prepared from polyether polyols which are preferably copolymerized by tetrahydrofuran and ethylene oxide in a molar ratio of 10: 1 to 1: 1, preferably 5: 1 to 3: 1 in the presence of strong acid, such as, for example, boron fluoride etherates getting produced.
• polyether polyols which, in addition to tetrahydrofuran units, also contain ethylene oxide units and / or propylene oxide units.
• the polyether polyols have at least 2 hydroxyl groups, but can also contain up to 20 hydroxyl groups per molecule.
• the molecular weights (M n ) of the polyether polyols used for the functionalization are usually in the range from 500 to 20,000 g / mol, preferably in the range from 2,000 to 10,000 g / mol.
• the functionalization with aziridino groups can be carried out, for example, by the process described in DE-C-1 745 810.
• Bis-aziridinopolyethers with aziridino equivalent masses of 2000 to 4000 g / equivalent are preferably used as component (A) to produce the soft dental compositions according to the invention, the polyether part preferably consisting of oxytetramethylene and oxydimethylene units in a ratio of 4: 1 to 3: 1 and the The proportion of oligomeric cyclic ethers in the bis'aziridino polyethers is less than 0.5% by weight, preferably less than 0.3% by weight.
• the impression materials contain 30 to 45% by weight to achieve the desired properties. of compounds that soften the hardened dental materials.
• Such compounds can be both typical plasticizers, such as are also offered for other polymeric systems, such as esters of polybasic carboxylic acids, polyaromatic compounds and sulfonic acid esters, or compounds which, in addition to softening, also have other effects, such as, for example, surfactant action, increasing the stability and improving the flow behavior ,
• the preparations according to the invention contain, according to component (B), three classes of compounds which cause the hardened dental materials to be softened, namely
• (B2) trisacylglycerides solid at room temperature with molecular weights in the range from 500 to 2000 g / mol
• phthalic acid esters of longer branched alcohols such as bis (2-ethylhexyl) phthalate or phthalic acid polyester
• C-2 to C-is dialkyl esters of C2 to C 6 dicarboxylic acids such as bis (2-ethylhexyl) adipate, dioctyl malate, diisopropyl
• aromatic and aliphatic sulfonic acid esters such as C 2 to C 20 alkyl sulfonic acid esters of phenol or of C to C-i ⁇ alkanols and typical aromatic plasticizers, such as: • polyphenyls in a wide viscosity range, including waxy ones
• An example of a preferred mixture is acetyl tributyl citrate and dibenzyl toluene.
• component (B2) trisacylesters of glycerol of non-animal origin are used.
• the component (B2) can consist of modified fats of vegetable origin, such as hydrogenated palm oil or soybean oil, or synthetic fats.
• Suitable fats are described in DE-A-197 11 514, to which full reference is made here.
• Particularly suitable are avocado oil, cottonseed oil, peanut oil, cocoa butter, pumpkin seed oil, linseed oil, corn oil, olive oil, palm oil, rice oil, rapeseed oils, safflower oil, sesame oil, soybean oil, sunflower oil, grapeseed oil, wheat germ oil, borneo, Fulwatalg, hemp oil, lllipebutter, Lupinienöle, Kandel nut oil, kapok oil , Katia fat, kenaf seed oil, kekuna oil, poppy seed oil, mowrah butter, okra oil, perillaol, sage butter, shea butter and tung oil, provided that these fats have been hardened before use.
• Suitable hardened fats are those whose iodine number (measured according to the DGF CV 11b standard) is less than 20. Fats whose iodine number is less than 5 are particularly preferred.
• the implementation of fat hardening is described, for example, in "Ullmann's Encyclopedia of Industrial Chemistry", 4th edition, volume 11, p. 469. Mixtures of these naturally occurring fats as well as artificially produced fats such as Softisan 154 or Dynasan 118 (from Hüls) can also be used.
• the preparation of such artificial triacylglycerides is relatively simple for the person skilled in the art and can be carried out, for example, from glycerol and the corresponding fatty acid methyl esters. Such esterification reactions are described, inter alia, in "Houben-Weyl, Methods of Organic Chemistry", Vol. E5 / Part 1, pp. 659 ff.
• Preferred triacylglycerides correspond to the formula:
• R 1 , R 2 and R 3 independently of one another are C 11 H 23 CO, C 13 H 27 CO, Ci ⁇ H 31 CO or C 17 H 35 CO. Mixtures of such triacylglycerides are also suitable.
• component (B2) of the present invention artificial fats with a steaoryl content of more than 65% by weight of the triglyceride are preferably used.
• liquid polymeric compounds in the preparations according to the invention have a particular effect.
• These compounds with molecular weights above 2000 g / mol can belong to different types of compounds, such as the polyether type, polyester type, polyurethane type, polycarbonate type, polyolefin type, hydroxyl, ether, alkyl and acyl groups being preferred as end groups.
• the end groups and possibly further functional groups are preferably selected such that no undesired reactions occur during the storage of the two components and after the mixture.
• Particularly preferred end groups are the primary and secondary OH groups and the acetyl group.
• a special class of compounds of liquid polymers are those of the polyether type.
• Bis-hydroxyl or bis-acetyl polyethers from oxytetramethylene and oxydimethylene units in a ratio of 4: 1 to 3: 1 and molar masses in the range from 3000 to 8000 g / mol and a proportion of oligomeric cyclic ethers of less than 0.5% by weight % are particularly preferred.
• polypropylene oxide polyols and / or copolymers and / or block copolymers of ethylene oxide and propylene oxide with hydroxyl or acetyl end groups can also be used.
• the preparations according to the invention contain, as component (C), 10 to 15% by weight of reinforcing fillers.
• organic and inorganic solids can be used which do not cause any undesired reactions in the substance mixtures of the respective component during the necessary storage and which do not impair the setting process after the separately stored components have been mixed.
• Fillers with an SiO 2 content of more than 90% by weight such as quartz powder and finely divided silicas of synthetic or natural origin, have proven particularly useful.
• Mixtures of processed diatomaceous earth with a pH value of the 5% aqueous suspension of 8 to 10 and pyrogenic, surface-modified silica with BET surface areas of 100 to 300 m 2 / g are particularly preferred fillers according to component (C).
• compositions according to the invention also comprise, according to component (D)
• the preparations according to the invention can be used in very different dental compositions used in dentistry or dental technology.
• Preferred areas of use for such dental materials are single-phase and two-phase dental impressions and bite registration.
• the invention also relates to containers and mixing devices containing compositions produced from the preparations according to the invention, in particular dental compositions, such as cartridges, bags, impression spoons, static and dynamic mixers or mixing devices.
• dental compositions such as cartridges, bags, impression spoons, static and dynamic mixers or mixing devices.
• a bis-aziridino polyether with a low content of cyclic oligomeric polyethers is prepared starting from a bis-aziridino polyether, which was obtained according to DE-C-174 58 10, according to preparation example 2 of DE-A-19740 234.
• the residual content of the cyclic oligomeric polyethers in this aziridinopolyether is determined by gas chromatography using the method described in DE-A-197 40 234.
• the table 1 characterized basic components produced on a laboratory kneader on a 500 g scale.
• the catalyst pastes characterized in Table 2 are produced in a laboratory kneader on a 100 g scale.
• the catalyst components and the base components were mixed in the stated ratio on the mixing block, the mixtures were transferred to a metal tray and the filled impression spoon was inserted into the subject's mouth.
• example 4 the impression tray was filled with the mass of example 3 according to the invention, whereas the test subject's teeth were extrusion-coated with the mass of example 4 according to the invention (double mixing technique).
• Comparative Example 3 the impression tray was filled with the mass of Comparative Example 1, the teeth of the subject, however, were extrusion-coated with the mass of Comparative Example 3 (double mixing technique).
• the removability of the impression from the subject's mouth was evaluated in accordance with the procedure described in DE-A-197 40 234 on eight subjects with different dentition situations by two performers and the subjective impressions were averaged.
• De-moldability was determined using a specially prepared lower jaw plastic model.
• the premolar 45 was provided with strong undercuts and included in the evaluation as an example of a single tooth, which was greatly reduced in substance due to periodontal damage.
• the plastic model was molded with the given impression preparations and the impressions obtained in this way were poured out with a stone plaster after an idle time of one hour.
• the demoldability was determined by three people. The three individual values were averaged.
• the Shore A hardness values of the inventive examples are in the desired range for soft impression materials (Shore A: 45 to 55, measured in accordance with DIN 53505).

Landscapes

• Health & Medical Sciences (AREA)
• Oral & Maxillofacial Surgery (AREA)
• Epidemiology (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Dental Preparations (AREA)
• Medicinal Preparation (AREA)

Priority Applications (6)

Applications Claiming Priority (2)

Publications (1)

Family

ID=7627782

Family Applications (1)

Country Status (7)

Cited By (3)

Families Citing this family (7)

Citations (5)

Family Cites Families (3)

• 2000
  • 2000-01-17 DE DE10001747A patent/DE10001747C2/de not_active Expired - Fee Related
• 2001
  • 2001-01-15 DE DE50106198T patent/DE50106198D1/de not_active Expired - Lifetime
  • 2001-01-15 EP EP01900446A patent/EP1248588B1/de not_active Expired - Lifetime
  • 2001-01-15 US US10/181,358 patent/US6919386B2/en not_active Expired - Lifetime
  • 2001-01-15 AT AT01900446T patent/ATE295142T1/de not_active IP Right Cessation
  • 2001-01-15 JP JP2001552842A patent/JP2003520216A/ja not_active Withdrawn
  • 2001-01-15 AU AU25160/01A patent/AU772056B2/en not_active Ceased
  • 2001-01-15 WO PCT/EP2001/000395 patent/WO2001052792A1/de not_active Ceased

Patent Citations (5)

Also Published As

Similar Documents

Legal Events