Dental curable composition and dental flowable composite resin

Patent metadata

Field	Value
Publication number	US-9855196-B2
Application number	US-201314648536-A
Country	US
Kind code	B2
Filing date	Nov 26, 2013
Priority date	Nov 30, 2012
Publication date	Jan 2, 2018
Grant date	Jan 2, 2018

Abstract

The present invention provides a dental curable composition suitable as a flowable composite resin. The dental curable composition, when in the form of a cured product, has excellent mechanical strength, polishability, and gloss retention, and, when in the form of a paste, has consistency appropriate for discharge through a needle attached to the tip of a syringe and exhibits good formability and handling properties after discharge through the needle. The present invention is a dental curable composition including: a polymerizable monomer (A); irregularly-shaped inorganic particles (B) having an average particle diameter of 0.1 to 0.3 μm and surface-treated with a silane coupling agent having a particular structure; and inorganic ultrafine particles (C) having an average particle diameter of 5 to 50 nm and surface-treated with a silane coupling agent having a particular structure, the dental curable composition containing 92.5 to 98 weight % of the irregularly-shaped inorganic particles (B) and 2 to 7.5 weight % of the inorganic ultrafine particles (C) relative to the amount of total inorganic particles and having a consistency of 25 to 55.

First claim

The invention claimed is:

1. A dental curable composition comprising:
a polymerizable monomer (A), which is a (meth)acrylic acid ester;
irregularly-shaped inorganic particles (B) having an average particle diameter of 0.1 to 0.3 μm and surface-treated with a silane coupling agent (a) represented by the following formula (1):
CH 2 ═C(R 1 )—COO—(CH 2 ) q —SiR 2 p R 3 (3-p)   (1),

 wherein R 1 represents a hydrogen atom or a methyl group, R 2 represents a hydrolyzable group, R 3 represents a hydrocarbon group having 1 to 6 carbon atoms, p is an integer of 2 or 3, and q is an integer of 8 to 13; and
inorganic ultrafine particles (C) having an average particle diameter of 5 to 50 nm and surface-treated with a silane coupling agent (b) represented by a formula that is the same as the formula (1) representing the silane coupling agent (a) except that q is an integer of 1 to 6,
wherein
the dental curable composition comprises 25 to 50 parts by weight of the polymerizable monomer (A), per 100 parts by weight of the amount of total inorganic particles,
the dental curable composition comprises 92.5 to 98 weight % of the irregularly-shaped inorganic particles (B) and 2 to 7.5 weight % of the inorganic ultrafine particles (C) relative to the amount of total inorganic particles, and
the dental curable composition has a consistency of 25 to 55.

2. The dental curable composition according to claim 1 , wherein the polymerizable monomer (A) has a refractive index after polymerization of 1.52 to 1.58, the irregularly-shaped inorganic particles (B) have a refractive index of 1.52 to 1.58, and the inorganic ultrafine particles (C) have a refractive index of 1.43 to 1.50.

3. The dental curable composition according to claim 1 , wherein the inorganic ultrafine particles (C) are present in the form of agglomerated particles, and the agglomerated particles have an average particle diameter of 1 to 10 μm.

4. A dental flowable composite resin comprising the dental curable composition according to claim 1 .

5. A package comprising a container holding the dental flowable composite resin according to claim 4 and a needle tip to be attached to a tip of the container.

6. A dental flowable composite resin comprising the dental curable composition according to claim 2 .

7. A dental flowable composite resin comprising the dental curable composition according to claim 3 .

8. A package comprising a container holding the dental flowable composite resin according to claim 6 and a needle tip to be attached to a tip of the container.

9. A package comprising a container holding the dental flowable composite resin according to claim 7 and a needle tip to be attached to a tip of the container.

10. The dental curable composition according to claim 1 , wherein the irregularly-shaped inorganic particles (B) are surface treated with at least one silane coupling agent selected from the group consisting of 11-methacryloyloxyundecyltrimethoxysilane, 8-methacryloyloxyoctyltrimethoxysilane, and 13-methacryloyloxytridecyltrimethoxysilane.

11. The dental curable composition according to claim 1 , wherein the inorganic ultrafine particles (C) are surface treated with 3-methacryloxypropyltrimethoxysilane.

12. The dental curable composition according to claim 1 , wherein the polymerizable monomer (A) is at least one selected from the group consisting of 2,2-bis(4-methacryloyloxypolyethoxyphenyl)propane, triethylene glycol dimethacrylate, 2,2-bis[4-(3-methacryloyloxy-2-hydroxypropoxy)phenyl]propane, 1,10-decanediol dimethacrylate, neopentyl glycol dimethacrylate, 1,6-hexanediol dimethacrylate, [2,2,4-trimethylhexamethylene bis(2-carbamoyloxyethyl)]dimethacrylate, and N,N′-(2,2,4-trimethylhexamethylene)bis[2-(aminocarboxy)propane-1,3-diol]tetramethacrylate.

13. The dental curable composition according to claim 1 , wherein
the irregularly-shaped inorganic particles (B) are surface treated with at least one silane coupling agent selected from the group consisting of 11-methacryloyloxyundecyltrimethoxysilane, 8-methacryloyloxyoctyltrimethoxysilane, and 13-methacryloyloxytridecyltrimethoxysilane,
the inorganic ultrafine particles (C) are surface treated with 3-methacryloxypropyltrimethoxysilane, and
the polymerizable monomer (A) is at least one selected from the group consisting of 2,2-bis(4-methacryloyloxypolyethoxyphenyl)propane, triethylene glycol dimethacrylate, 2,2-bis[4-(3-methacryloyloxy-2-hydroxypropoxy)phenyl]propane, 1,10-decanediol dimethacrylate, neopentyl glycol dimethacrylate, 1,6-hexanediol dimethacrylate, [2,2,4-trimethylhexamethylene bis(2-carbamoyloxyethyl)]dimethacrylate, N,N′-(2,2,4-trimethylhexamethylene)bis[2-(aminocarboxy)propane-1,3-diol]tetramethacrylate.

14. The dental curable composition according to claim 1 , wherein R 2 of formula (1) represents an alkoxy group.

15. The dental curable composition according to claim 1 , wherein q is 3 for the silane coupling agent (b).

16. The dental curable composition according to claim 1 , wherein
R 2 of formula (1) represents an alkoxy group, and
q is 3 for the silane coupling agent (b).

Assignees

• Kuraray Noritake Dental Inc

Inventors

• Kameya Takehiro
• Ishino Hiroshige
• Tsuji Akiko

Classifications

• A61K6/20

  Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish · CPC title

• A61K6/831

  comprising non-metallic elements or compounds thereof, e.g. carbon · CPC title

• A61K6/17

  Particle size · CPC title

• A61K6/836

  Glass · CPC title

• A61K6/16 Primary

  Refractive index · CPC title