EP-4736835-A1 - DENTAL POLYMERIZABLE COMPOSITION

Abstract

The present invention provides a dental polymerizable composition that exhibits excellent toughness and water resistance in the cured product while reducing leachables from the cured product. The present invention relates to a dental polymerizable composition that comprises a polyfunctional (meth)acrylic polymerizable compound (A), and a photopolymerization initiator (B) containing no phosphine oxide framework. Preferably, the photopolymerization initiator (B) containing no phosphine oxide framework comprises a Norrish Type II photopolymerization initiator. Preferably, the polyfunctional (meth)acrylic polymerizable compound (A) comprises a polyfunctional (meth)acrylic polymerizable compound (A)-I having a molecular weight of less than 1,000, and/or a polyfunctional (meth)acrylic polymerizable compound (A)-II having a molecular weight of 1,000 or more.

Inventors

• SUZUKI, KENJI

Assignees

• Kuraray Noritake Dental Inc.

Dates

Publication Date

20260506

Application Date

20240628

Claims (17)

1. A dental polymerizable composition comprising a polyfunctional (meth)acrylic polymerizable compound (A), and a photopolymerization initiator (B) containing no phosphine oxide framework.
2. The dental polymerizable composition according to claim 1, wherein the photopolymerization initiator (B) containing no phosphine oxide framework comprises a Norrish Type II photopolymerization initiator.
3. The dental polymerizable composition according to claim 1 or 2, wherein the polyfunctional (meth)acrylic polymerizable compound (A) comprises a polyfunctional (meth)acrylic polymerizable compound (A)-I with a molecular weight of less than 1,000, and/or a polyfunctional (meth)acrylic polymerizable compound (A)-II with a molecular weight of 1,000 or more.
4. The dental polymerizable composition according to claim 3, wherein the polyfunctional (meth)acrylic polymerizable compound (A) comprises a polyfunctional urethanized (meth)acrylic polymerizable compound (A)-I-1 that contains a urethane bond and has a molecular weight of less than 1,000, and/or a polyfunctional urethanized (meth)acrylic polymerizable compound (A)-II-1 that contains a urethane bond and has a molecular weight of 1,000 or more.
5. The dental polymerizable composition according to claim 4, wherein the polyfunctional (meth)acrylic polymerizable compound (A)-I-1 comprises a (meth)acrylate that contains no polymeric structure within a single molecule.
6. The dental polymerizable composition according to claim 4, wherein the polyfunctional urethanized (meth)acrylic polymerizable compound (A)-II-1 comprises a (meth)acrylate that comprises, within a single molecule, at least one structure selected from the group consisting of a polyester, a polycarbonate, a polyurethane, a polyether, a poly-conjugated diene, and a hydrogenated poly-conjugated diene.
7. The dental polymerizable composition according to claim 4, wherein the polyfunctional urethanized (meth)acrylic polymerizable compound (A)-II-1 comprises a (meth)acrylate that comprises, within a single molecule, at least one polyol moiety selected from the group consisting of a polyester, a polycarbonate, a polyurethane, a polyether, a poly-conjugated diene, and a hydrogenated poly-conjugated diene each having a structure derived from a C4 to C18 aliphatic chain diol unit having a branched structure.
8. The dental polymerizable composition according to claim 1 or 2, wherein the photopolymerization initiator (B) containing no phosphine oxide framework comprises at least one selected from the group consisting of an α-aminoketone compound, an oxime ester compound, and a thioxanthone.
9. The dental polymerizable composition according to claim 1 or 2, which further comprises a monofunctional (meth)acrylic polymerizable compound (C).
10. The dental polymerizable composition according to claim 9, wherein the monofunctional (meth)acrylic polymerizable compound (C) comprises a monofunctional (meth)acrylic polymerizable compound (C)-I containing a cyclic structure.
11. The dental polymerizable composition according to claim 10, wherein the monofunctional (meth)acrylic polymerizable compound (C)-I comprises one or more aromatic rings.
12. The dental polymerizable composition according to claim 10, wherein the monofunctional (meth)acrylic polymerizable compound (C)-I comprises a plurality of aromatic rings.
13. A stereolithographic material comprising a dental polymerizable composition of claim 1 or 2.
14. A denture base material comprising a cured product of a stereolithographic material of claim 13.
15. A dental occlusal splint comprising a cured product of a stereolithographic material of claim 13.
16. A material for treating sleep disorder, comprising a cured product of a stereolithographic material of claim 13.
17. A method for stereolithographically producing a three-dimensional shaped article using a dental polymerizable composition of claim 1 or 2.

Description

TECHNICAL FIELD The present invention relates to dental polymerizable compositions, particularly stereolithographic dental polymerizable compositions formulated with a large amount of photopolymerization initiator. More specifically, the invention relates to a dental polymerizable composition that allows for the formation of a cured product with superior strength, toughness, water resistance, and color tone while achieving excellent biological safety with reduced amounts of leachables from the cured product. The invention is suited for stereolithographic materials used in dentistry, with optimum suitability for dental occlusal splints, denture base materials, and appliances for the treatment of sleep apnea. BACKGROUND ART Dental polymerizable compositions are employed in a variety of applications, including restorative filling materials for tooth defects or carious cavities, adhesives for securing such restorative filling materials to teeth, metal or ceramic crown restoration materials called inlays or crowns, luting agents for securing such crown restoration materials to teeth, and dental materials such as those for dental occlusal splints or denture bases. Typically, dental polymerizable compositions contain (meth)acrylic polymerizable monomers, polymerization initiators, and, optionally, fillers such as inorganic compounds, in addition to other optional additives. The polymerization initiators used in such applications include photopolymerization initiators and chemical polymerization initiators. Dental polymerizable compositions fall into the following broad categories: photopolymerizable compositions formulated with photopolymerization initiators, chemical polymerizable compositions formulated with chemical polymerization initiators, and compositions that exhibit both photopolymerizable and chemical polymerizable properties by incorporating both types of initiators. Photopolymerization initiators are indispensable in most dental materials. Various proposals have been made concerning optical 3D fabrication (stereolithography), a method that produces three-dimensional shaped articles through a repeated procedure whereby liquid photocurable resin composition containing a photopolymerization initiator is cured into a thin layer under controlled application of necessary amounts of light energy, and another thin layer is cured on the cured layer under controlled application of light after supplying another portion of the liquid photocurable composition onto the previously formed cured layer. Vat stereolithography is a technique typically used for optical fabrication of three-dimensional shaped articles. In this technique, a liquid photocurable composition is placed in a vat, and a computer-controlled ultraviolet laser is selectively applied to the surface of the liquid photocurable composition to cure it to a predetermined thickness, forming a cured layer with the desired pattern. Continuously, another cured layer is formed on the cured layer by applying an ultraviolet laser in the same manner to the liquid photocurable composition supplied onto the previously cured layer in an amount necessary to form a single layer. This layering process is repeated until it produces the final three-dimensional shaped article. In recent years, this technique has attracted great interest because it enables easy and precision production of the desired three-dimensional shaped article in a relatively short time period, even when the article has a very complex shape. Three-dimensional shaped articles created through stereolithography are expanding their applications from mere concept models to test models, prototypes, and final products. The field of dental materials is thought to greatly benefit from stereolithography because dental occlusal splints, denture bases, and mouthpiece-like materials used for treating sleep disorders (for example, appliances for preventing bruxism or treating sleep apnea) require shapes that vary from patient to patient, aside from being complex in shape. Some dental occlusal splints are fitted to adjust tooth alignment or jaw position as in so-called orthodontic mouthpieces or aligners while others are attached to teeth to reduce tooth wear due to clenching. Mouthguards are another type of splints that are worn in the mouth to protect the stomatognathic system and the brain by reducing injuries caused when large external forces are applied to teeth and jawbones during sports activities in contact sports. In orthodontics, the use of these devices has gained wide popularity over the last years due to their favorable aesthetics and convenient removability. Denture base materials are materials used for the gum as a part of a denture attached to replace missing teeth. The demand for dentures has rapidly increased in recent years because of increasing ageing populations. Appliances for the treatment of sleep apnea include appliances (oral appliances, or OA) attached to teeth during sleep for the treatme