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Polymerizable monomer-containing composition

a polymerizable monomer and composition technology, applied in dental prosthetics, impression caps, coatings, etc., can solve problems such as reducing bond strength, and achieve excellent curability and adhesive properties, high bond strength and bond durability, and high penetration

Inactive Publication Date: 2010-02-25
KURARAY MEDICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0061]The composition of the present invention is characterized by containing 6 to 2000 parts by weight of water (B) with respect to 100 parts by weight of the whole amount of polymerizable monomer components. Since the composition of the present invention contains such amount of the water (B) to be added, when it is used as a dental composition, it exhibits both excellent bond strength and excellent bond durability. When the amount of the water (B) to be added is less than 6 parts by weight, penetrability of the monomer into a collagen layer becomes insufficient, thereby causing reduction in bond strength. The amount of the water (B) to be added is preferably at least 7 parts by weight, more preferably at least 8 parts by weight, further preferably at least 10 parts by weight. On the other hand, when the amount of the water (B) to be added exceeds 2000 parts by weight, polymerizability of the monomer is reduced, causing reduction of the bond strength as well as bond durability. Therefore, the amount of the water (B) to be added should be 2000 parts by weight or less, preferably 1500 parts by weight or less. In fact, as seen from the comparison of Example 1 and 2 in the below described examples to Comparative example 1, when the amount of the water (B) to be added is less than 6 parts by weight, sufficiently high bond strength cannot be obtained. Thus, it was confirmed that when the amount of the water (B) to be added is in a specific range, the advantageous effects of the present invention can be obtained. Further, it is preferable that the water (B) be free from impurity that can cause any adverse effects, and be distilled water or ion-exchanged water. The water (B) may be used independently, or it may be used in the form of a mixed solvent of the water (B) and an organic solvent (E) that will be described later.
[0062]Next, arbitrary components of the composition according to the present invention are described. The composition of the present invention may contain components other than the polymerizable monomer (A) and the water (B) depending on the application of the composition. For instance, the composition of the present invention may contain, as a polymerizable monomer component other than the polymerizable monomer (A), polymerizable monomer components such as a polymerizable monomer (C) having an acidic group, and a crosslinkable polymerizable monomer (D). Preferably, the polymerizable groups included in these polymerizable monomers are groups that are radical-copolymerizable with polymerizable groups of the polymerizable monomer (A).
[0063]Furthermore, the composition of the present invention may contain an organic solvent (E), a polymerization initiator (F), a polymerization accelerator (G), and a filler (H).
[0064]In the present invention, the phrase “the whole amount of polymerizable monomer components” denotes the total amount of the polymerizable monomer (A), the polymerizable monomer (C), and the polymerizable monomer (D).
[0066]Preferably, the composition of the present invention contains 1 to 90 parts by weight of polymerizable monomer (C) having an acidic group in 100 parts by weight of the whole amount of polymerizable monomer components. When a composition in which the amount of polymerizable monomer (C) having an acidic group to be added is in such a range is used as a dental composition, it has advantages that, for example, pretreatments such as an acid etching treatment and a primer treatment are not necessary, since the polymerizable monomer (C) itself that has an acidic group has an acid-etching effect and a primer treatment effect. Accordingly, a combination with a polymerizable monomer (C) having an acidic group makes it possible to provide a bonding material that is simple to use and has high bond strength and excellent bond durability, particularly preferably a one-component bonding material. When the amount of polymerizable monomer (C) having an acidic group to be added is less than 1 part by weight, the acid-etching effect or primer treatment effect may not be obtained. Therefore, the amount is more preferably at least 2 parts by weight and further preferably at least 5 parts by weight. On the other hand, when the amount of polymerizable monomer (C) having an acidic group to be added exceeds 90 parts by weight, sufficiently high curability may not be obtained and therefore the adhesive properties may be deteriorated. Accordingly, the amount is more preferably 80 parts by weight or less and further preferably 70 parts by weight or less.
[0067]Polymerizable monomers (C) having acidic groups can be used independently or two or more of them can be used in suitable combination. The polymerizable monomers (C) having acidic groups are not particularly limited. Examples thereof include a monofunctional polymerizable monomer having one carboxyl group or an acid anhydride group thereof in the molecule, a monofunctional polymerizable monomer having a plurality of carboxyl groups or an acid anhydride group thereof in the molecule, and a monofunctional polymerizable monomer having a phosphinyloxy group or phosphonooxy group in the molecule (also referred to as a monofunctional radical polymerizable phosphoric acid ester).

Problems solved by technology

This composition is, however, not necessarily excellent in penetrability into a collagen layer of dentin and may cause a reduction in bond strength, and therefore improvement in this respect has been desired.

Method used

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  • Polymerizable monomer-containing composition
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Examples

Experimental program
Comparison scheme
Effect test

example 1

Application to One-Step Bonding System (One-Component Bonding Material)

(1) Production of One-Component Bonding Material

[0159]Respective components were mixed together at an ordinary temperature and thereby a one-component bonding material composition was produced. The composition thereof is indicated in Table 1. The bond strength with respect to bovine teeth dentin was measured according to the following procedure.

TABLE 1One-Component Bonding Material Compositions and Bonding Evaluation ResultsEx.Ex.Ex.Ex.Ex.Ex.Ex.C Ex.C. Ex.C. Ex.C. Ex.C. Ex.C. Ex.C. Ex.Components1-11-21-31-41-51-61-71-11-21-31-41-51-61-7PolymerizableEDMA3030153030monomer (A)XDMA30SDMA30MDMA303015Polymerizable#80130monomer forGDMA3030comparisonErMA30with (A)Trimethylol-30propane tri-methacrylateWater (B)Distilled water15151515151515215001515151515PolymerizableMDP1010101010101010101010101010monomer (C)having acidicgroupCrosslinkableBis-GMA3030303030303030303030303030polymerizablemonomer (D)Solvent (E)Ethanol15151515...

example 2

Application to Two-Step Bonding System (Two-Component Bonding Material)

(1) Production of Primer Using Polymerizable Composition Containing Polymerizable Monomer (A)

[0172]The respective components were mixed together at ordinary temperature and thereby primer compositions were produced. The compositions thereof are indicated in Table 2.

TABLE 2Primer Compositions and Bonding Evaluation ResultsEx.Ex.Ex.Ex.Ex.Ex.Ex.C. Ex.C. Ex.C. Ex.C. Ex.Components2-12-22-32-42-52-62-72-12-22-32-4PlymerizableEDMA3535703535monomer (A)XDMA35SDMA35MDMA3535PolymerizableGDMA3535monomer forErMA35comparisonwith (A)Water (B)Distilled water50505050505050315005050PolymerizableMDP2020202020202020202020monomer (C)having acidicgroupCrosslinkable#8011010101010101010101010polymerizablemonomer (D)Solvent (E)Ethanol5050505050505095505050PolymerizationTMDPO0.80.80.80.80.80.80.80.80.80.8initiator (F)CQ0.8PolymerizationDBB1accelerator (G)Ratio of water (B) with respect77777777775050523077777to 100 parts by weight of thewh...

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Abstract

The present invention provides a composition suitable for a dental composition. The present invention is a composition containing: a polymerizable monomer (A) having an unconjugated carbon chain with at least four carbon atoms bonded continuously, at least two polymerizable groups, and at least two hydroxyl groups; and a water (B). The composition contains 6 to 2000 parts by weight of the water (B) with respect to 100 parts by weight of the whole amount of polymerizable monomer components. When suitable components are added to this composition, the resultant composition can be used suitably for dental materials such as a primer, bonding material, composite resin, and cement.

Description

TECHNICAL FIELD[0001]The present invention relates to a composition containing: a bifunctional polymerizable monomer having polymerizable groups and hydroxyl groups; and water.BACKGROUND ART[0002]When a lost part of a tooth is filled or covered with a restorative material, generally a dental adhesive is used. A known dental adhesive is one containing a polymerizable monomer having a polymerizable group and a hydroxyl group.[0003]For example, WO 2004 / 047773 describes a dental adhesive composition characterized by containing a polyfunctional polymerizable monomer that is an ester compound of polyhydric alcohol having 3 to 6 carbon atoms and a plurality of (meth)acrylic acids and that has one to two hydroxyl groups, a monofunctional (meth)acrylate having no hydroxyl group in the molecule, a polymerizable monomer having an acidic group in the molecule, an organoboron compound as a curing agent, and a filling material. This describes that the addition of a small amount of the above polyf...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08F118/02C08L33/02A61K6/083A61K6/884A61K6/891A61K6/898
CPCA61K6/0023A61K6/083C08F20/10C08F20/28C08F220/26C08L33/04C08L33/26A61K6/30A61K6/887
Inventor ISHINO, HIROSHIGESEKIGUCHI, TAKAHIROOKADA, KOICHI
Owner KURARAY MEDICAL
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