Two-paste dental curable composition

Patent metadata

Field	Value
Publication number	US-11400030-B2
Application number	US-201816626675-A
Country	US
Kind code	B2
Filing date	Jun 28, 2018
Priority date	Jun 28, 2017
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

The present invention provides a two-paste dental curable composition achieving clinically acceptable bond durability to dental adherends including dental glass ceramic restorations (particularly lithium disilicate-containing glass ceramic restorations) without using conventionally used primers. The present invention relates to a two-paste dental curable composition comprising: a first agent comprising a polymerizable monomer (a) having an acid group, a polymerizable monomer (b) having no acid group, a polymerization initiator (c), and a filler (d); and a second agent comprising a polymerizable monomer (b) having no acid group, at least one filler (e) selected from the group consisting of a basic glass filler and alumina, a polymerization accelerator (f), and a silane coupling agent (g) represented by the following general formula [I]:

(The definitions of the symbols are omitted.)

First claim

The invention claimed is:

1. A two-paste dental curable composition, comprising:
a first agent comprising a polymerizable monomer (a) comprising an acid group, a polymerizable monomer (b) having no acid group, a polymerization initiator (c), and a filler (d); and
a second agent comprising a polymerizable monomer (b) comprising no acid group, at least one filler (e) selected from the group consisting of a lanthanum glass, barium glass, strontium glass, soda glass, zinc glass, fluoroaluminosilicate glass, and alumina, a polymerization accelerator (f), and a silane coupling agent (g) of formula (I):

wherein
X is a polymerizable (meth)acryloxy group, vinyl group, or epoxy group,
R 1 is a divalent aliphatic group optionally comprising a divalent group and comprising a linear chain with a carbon chain length of 5 or more or a divalent aromatic group optionally comprising a divalent group and comprising 6 or more carbon atoms,
R 2 , R 3 , and R 4 are each independently a hydroxy group, an alkyl group comprising 1 to 5 carbon atoms, or an alkoxy group comprising I to 5 carbon atoms, and at least one of R 2 , R.', and R 4 is an alkoxy group comprising 1 to 5 carbon atoms,
wherein, in the first agent, the polymerization initiator (c) comprises an inorganic peroxide (c-1) or a transition metal complex (c-2). the inorganic peroxide (c-1) comprising at least one selected from the group consisting of peroxodisulfuric acid salt and peroxodiphosphoric acid salt, and the transition metal complex (c-2) comprising at least one selected from the group consisting of a copper compound and vanadium compound.

2. The composition of claim 1 , wherein R 1 is a divalent aliphatic group optionally comprising a divalent group and comprising a linear chain with a carbon chain length of 7 or more or a divalent aromatic group optionally comprising a divalent group and comprising 7 or more carbon atoms.

3. The composition of claim 1 , wherein
R 2 , R 3 , and R 4 are each independently a hydroxy group, an alkyl group comprising 1 to 3 carbon atoms, or an alkoxy group comprising 1 to 3 carbon atoms and
at least one of R 2 , R 3 , and R 4 is an alkoxy group comprising 1 to 3 carbon atoms.

4. The composition of claim 1 , wherein
R 2 , R 3 , and R 4 are each independently a hydroxy group, a methyl group, or a methoxy group, and
at least one of R 2 , R 3 , and R 4 is a methoxy group.

5. The composition of claim 1 , wherein R 2 , R 3 , and R 4 are each a methoxy group.

6. The composition of claim 1 , wherein R 1 is a divalent aliphatic group optionally comprising a divalent group and comprising a linear chain with a carbon chain length of 8 or more.

7. The composition of claim 1 , wherein R 1 is a divalent aromatic group optionally comprising a divalent group and comprising 8 or more carbon atoms.

8. The composition of claim I, wherein the silane coupling agent (g) is at least one selected from the group consisting of 5-(meth)acryloxypentyltrimethoxysilane, 6-(meth)acryloxyhexyltrimethoxysilane, 7-(meth)acryloxyheptyltrimethoxysilane, 8-(meth)acryloxyoctyltrimethoxysilane, 9-(meth)acryloxyrionyhrimethoxysilane, 10-(meth)acryloxydecyltrimethoxysilane, 11-(meth)acryloxyundecyltrimethoxysilane, 8-(meth)acryloxyoctylmethyldimethoxysilane, 10-(meth)acryloxydecylmethyldimethoxysilane, 11-(meth)acryloxyundecylmethyldimethoxysilane, and (meth)acryloxymethylphenethyltrimethoxysilane.

9. The composition of claim 1 , wherein the silane coupling agent (g) is at least one selected from the group consisting of 8-(meth)acryloxyoctyltrimethoxysilane, 9-(meth)acryloxynonyltrimethoxysilane, 10-(meth)acryloxydecyltrimethoxysilane, 11-(meth)acryloxyundecyltrimethoxysilane, and (meth)acryloxymethylphenethyltrimethoxysilane.

10. The composition of claim 1 , wherein the second agent further comprises a crosslinking agent (h), and
wherein the crosslinking agent (h) is a compound of formula (V):

and/or
a compound of formula (V1):

wherein
R 8 is a divalent aliphatic group optionally comprising a divalent group and having a carbon chain length of 1 or more or a divalent aromatic group optionally comprising a divalent group and comprising 6 or more carbon atoms,
R 15 is a trivalent aliphatic group having a carbon chain length of 1 or more or a trivalent aromatic group optionally comprising a divalent group and comprising 6 or more carbon atoms, and
R 5 to R 7 , R 9 to R 14 , and R 16 to R 21 are each independently a hydroxy group or an alkoxy group comprising 1 to 5 carbon atoms.

11. The composition of claim 10 , wherein
R 8 is a divalent aromatic group optionally comprising a divalent group and comprising 6 or more carbon atoms and
R 15 is a trivalent aromatic group optionally comprising a divalent group and comprising 6 or more carbon atoms.

12. The composition of claim 10 , wherein the crosslinking agent (h) is the compound of formula (V), and
wherein R 8 is a divalent aliphatic group optionally comprising a divalent group and having a carbon chain length of 1 or more.

13. The composition of claim 1 , wherein the first agent further comprises a silanol condensation catalyst (i) of formula (VII):
M(R 22 ) n (VII), wherein
M is Ti, Zr, or Al,
R 22 is an aliphatic group,
n is an integer in a range of from 1 to 4plural R 22 optionally differing from each other.

14. The composition of claim 13 , wherein R 22 is an alkoxy group comprising 1 to 9 carbon atoms, an acyloxy group comprising 2 to 9 carbon atoms, an alkenyloxy group comprising 3 to 9 carbon atoms, a β-diketonate group comprising 5 to 15 carbon atoms, or a diacylmethyl group having acyl groups each comprising 1 to 9 carbon atoms.

15. The composition of claim 1 , wherein the first agent and/or the second agent further comprises a photopolymerization initiator (j).

16. The composition of claim 1 , wherein the filler (e) is the barium glass and/or the alumina.

17. The composition of claim 1 , which is suitable for application to a biological hard tissue.

18. The composition of claim 1 , a tensile bond strength to lithium disilicate glass ceramic at a temperature of 70° C. after 3 days in a range of from 16.2 to 28,5 MPa.

19. The composition of claim 1 , wherein the silane coupling agent (g) comprises 8-(meth)acryloxyoctyltrimethoxyvsilane, 9-(meth)acryloxynonyltrimethoxysilane, 10-(meth)acryloxydecyltrimethoxysilane, 11-(meth)acryloxyundecyltrimethoxysilane, and/or (meth)acryloxymethylphenethylnimethoxysilane.

20. A two-paste dental curable composition, comprising:
a first agent comprising (a) a polymerizable monomer comprising an acid group, (b) a polymerizable monomer having no acid group, (c) a polymerization initiator, and (d) a filler; and
a second agent comprising (b) a polymerizable monomer comprising no acid group, (e) a basic glass filler and alumina, (f) a polymerization accelerator, and (g) a silane coupling agent of formula (1):

wherein
X is a polyrnerizable (meth)acryloxy group, vinyl group, or epoxy group,
R 1 is a divalent aliphatic group opti

Assignees

• Kuraray Noritake Dental Inc

Inventors

• KAWANA Mariko
• Hatanaka Kenji
• ABE Momoe

Classifications

• C08F222/1025

  of aromatic dialcohols · CPC title

• C08F2/50 Primary

  with sensitising agents · CPC title

• A61K6/30

  Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives · CPC title

• C08K3/36

  Silica · CPC title

• A61K6/887 Primary

  Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title