Dental adhesive composition including chain transfer agent

Patent metadata

Field	Value
Publication number	US-11033465-B2
Application number	US-201916357377-A
Country	US
Kind code	B2
Filing date	Mar 19, 2019
Priority date	Mar 20, 2018
Publication date	Jun 15, 2021
Grant date	Jun 15, 2021

Abstract

To provide a one paste type dental adhesive composition which has mechanical characteristics and aesthetic property required in the restoration material, is superior in durable adhesive strength to the tooth substance, and is hard to be affected by the polymerization shrinkage stress and exhibits excellent durable adhesive strength even if the composition of the present invention is collectively filled and cured.
To provide a dental adhesive composition comprising: (a) an acidic group-non-containing polymerizable monomer, (b) an acidic group-containing polymerizable monomer, (c) a filler, (d) a photo polymerization initiator, and (e) a chain transfer agent, wherein the chain transfer agent (e) contains α-alkylstyrene compound.

First claim

What is claimed is:

1. A one paste dental adhesive composition comprising:
(a) an acidic group-non-containing polymerizable monomer,
(b) an acidic group-containing polymerizable monomer,
(c) a filler,
(d) a photo polymerization initiator, and
(e) a chain transfer agent, wherein
the chain transfer agent (e) contains an α-alkylstyrene compound.

2. The one paste dental adhesive composition according to claim 1 , wherein
the one paste dental adhesive composition comprises the acidic group-non-containing polymerizable monomer (a) and the acid group-containing polymerizable monomer (b) in a weight ratio of the acidic group-non-containing polymerizable monomer (a): the acid group-containing polymerizable monomer (b)=99:1 to 70:30.

3. The one paste dental adhesive composition according to claim 2 , wherein
the one paste dental adhesive composition comprises
0.01 to 10 parts by weight of the photo polymerization initiator (d) and 0.01 to 5 parts by weight of the chain transfer agent (e) based on 100 parts by weight of a total content of a polymerizable monomer component consisting of the acidic group-non-containing polymerizable monomer (a) and the acidic group-containing polymerizable monomer (b), and
50 to 900 parts by weight of the filler (c) based on 100 parts by weight a total content of a resin component consisting of the acidic group-non-containing polymerizable monomer (a), the acidic group-containing polymerizable monomer (b), the photo polymerization initiator (d) and the chain transfer agent (e).

4. The one paste dental adhesive composition according to claim 1 , wherein
the one paste dental adhesive composition comprises 5 to 70 parts by weight of (f) an acidic group-non-containing hydrophilic polymerizable monomer in 100 parts by weight of the acidic group-non-containing polymerizable monomer (a).

5. The one paste dental adhesive composition according to claim 1 , wherein
the chain transfer agent (e) is 2,4-diphenyl-4-methyl-1-pentene.

6. The one paste dental adhesive composition according to claim 1 , wherein
a relationship between a refractive index na of a resin component consisting of the acidic group-non-containing polymerizable monomer (a), the acidic group-containing polymerizable monomer (b), the photo polymerization initiator (d) and the chain transfer agent (e) before curing and a refractive index nc of the filler (c) satisfies the following formula (1):
| na−nc|≤ 0.01  (1).

7. The one paste dental adhesive composition according to claim 2 , wherein
the one paste dental adhesive composition comprises 5 to 70 parts by weight of (f) an acidic group-non-containing hydrophilic polymerizable monomer in 100 parts by weight of the acidic group-non-containing polymerizable monomer (a).

8. The one paste dental adhesive composition according to claim 3 , wherein
the one paste dental adhesive composition comprises 5 to 70 parts by weight of (f) an acidic group-non-containing hydrophilic polymerizable monomer in 100 parts by weight of the acidic group-non-containing polymerizable monomer (a).

9. The one paste dental adhesive composition according to claim 2 , wherein
the chain transfer agent (e) is 2,4-diphenyl-4-methyl-1-pentene.

10. The one paste dental adhesive composition according to claim 3 , wherein
the chain transfer agent (e) is 2,4-diphenyl-4-methyl-1-pentene.

11. The one paste dental adhesive composition according to claim 4 , wherein
the chain transfer agent (e) is 2,4-diphenyl-4-methyl-1-pentene.

12. The one paste dental adhesive composition according to claim 2 , wherein
a relationship between a refractive index na of a resin component consisting of the acidic group-non-containing polymerizable monomer (a), the acidic group-containing polymerizable monomer (b), the photo polymerization initiator (d) and the chain transfer agent (e) before curing and a refractive index nc of the filler (c) satisfies the following formula (1):
| na−nc|≤ 0.01  (1).

13. The one paste dental adhesive composition according to claim 3 , wherein
a relationship between a refractive index na of the resin component consisting of the acidic group-non-containing polymerizable monomer (a), the acidic group-containing polymerizable monomer (b), the photo polymerization initiator (d) and the chain transfer agent (e) before curing and a refractive index nc of the filler (c) satisfies the following formula (1):
| na−nc|≤ 0.01  (1).

14. The one paste dental adhesive composition according to claim 4 , wherein
a relationship between a refractive index na of a resin component consisting of the acidic group-non-containing polymerizable monomer (a), the acidic group-containing polymerizable monomer (b), the photo polymerization initiator (d) and the chain transfer agent (e) before curing and a refractive index nc of the filler (c) satisfies the following formula (1):
| na−nc|≤ 0.01  (1).

15. The one paste dental adhesive composition according to claim 5 , wherein
a relationship between a refractive index na of a resin component consisting of the acidic group-non-containing polymerizable monomer (a), the acidic group-containing polymerizable monomer (b), the photo polymerization initiator (d) and the chain transfer agent (e) before curing and a refractive index nc of the filler (c) satisfies the following formula (1):
| na−nc|≤ 0.01  (1).

16. A dental adhesive composition comprising:
(a) an acidic group-non-containing polymerizable monomer,
(b) an acidic group-containing polymerizable monomer,
(c) a filler,
(d) a photo polymerization initiator,
(e) a chain transfer agent, and
(f) an acidic group-non-containing hydrophilic polymerizable monomer, wherein
the chain transfer agent (e) contains an α-alkylstyrene compound, and
the dental adhesive composition comprises 5 to 70 parts by weight of the (f) an acidic group-non-containing hydrophilic polymerizable monomer in 100 parts by weight of the acidic group-non-containing polymerizable monomer (a).

17. The dental adhesive composition according to claim 16 , wherein
the dental adhesive composition comprises the acidic group-non-containing polymerizable monomer (a) and the acid group-containing polymerizable monomer (b) in a weight ratio of the acidic group-non-containing polymerizable monomer (a): the acid group-containing polymerizable monomer (b)=99:1 to 70:30.

18. The dental adhesive composition according to claim 16 , wherein
the dental adhesive composition comprises
0.01 to 10 parts by weight of the photo polymerization initiator (d) and 0.01 to 5 parts by weight of the chain transfer agent (e) based on 100 parts by weight of a total content of a polymerizable monomer component consisting of the acidic group-non-containing polymerizable monomer (a) and the acidic group-containing polymerizable monomer (b), and
50 to 900 parts by weight of the filler (c) based on 100 parts by weight a total content of a resin component consisting of the acidic group-non-containing polymerizable monomer (a), the acidic group-containing polymerizable monomer (b), the photo polymerization initiator (d) and the chain transfer agent (e).

19. The dental adhesive composition according to claim 16 , wherein
the chain transfer agent (e) is 2,4-diphenyl-4-methyl-1-pentene.

20. The dental adhesive composition according to claim 16 , wherein
a relationship between a refractive index na of a resin component consisting of the acidic group-non-containing polymerizable monomer (a), the acidic group-containing polymerizable monomer (b),

Assignees

• Shofu Inc

Inventors

• Miyata Shunsuke
• Fujimura Hidefumi

Classifications

• A61K6/62 Primary

  Photochemical radical initiators · CPC title

• A61K6/71

  Fillers · CPC title

• A61K6/30 Primary

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