One-part dental adhesive

Patent metadata

Field	Value
Publication number	US-9700491-B2
Application number	US-201314387396-A
Country	US
Kind code	B2
Filing date	Mar 15, 2013
Priority date	Mar 30, 2012
Publication date	Jul 11, 2017
Grant date	Jul 11, 2017

Abstract

The present invention provides a one-part dental adhesive that exhibits excellent adhesive properties to both enamel and dentin and that has high storage stability and ambient-light stability. The present invention is a one-part dental adhesive including 1 to 30 weight % of a phosphoric acid group-containing monofunctional (meth)acrylate compound (a), 10 to 50 weight % of a water-soluble polymerizable monomer (b), 5 to 50 weight % of a hydrophobic crosslinkable (meth)acrylate compound (c), water (d), and a polymerization initiator (e). The water-soluble polymerizable monomer (b) includes a combination of a monofunctional (meth)acrylamide compound (b-1) having a particular structure and a water-soluble crosslinkable (meth)acrylic monomer (b-2). The weight ratio between the monofunctional (meth)acrylamide compound (b-1) and the water-soluble crosslinkable (meth)acrylic monomer (b-2) is 10:1 to 1:5.

First claim

The invention claimed is:

1. A one-part dental adhesive comprising:
1 to 30 weight % of a phosphoric acid group-containing monofunctional (meth)acrylate compound (a);
10 to 50 weight % of a water-soluble polymerizable monomer (b);
5 to 50 weight % of a hydrophobic crosslinkable (meth)acrylate compound (c);
water (d); and
a polymerization initiator (e), wherein
the water-soluble polymerizable monomer (b) consists of a monofunctional (meth)acrylamide compound (b-1) and a water-soluble crosslinkable (meth)acrylic monomer (b-2),
a weight ratio between the monofunctional (meth)acrylamide compound (b-1) and the water-soluble crosslinkable (meth)acrylic monomer (b-2) is 10:1 to 1:5, and
the monofunctional (meth)acrylamide compound (b-1) is represented by the following formula (1):

where R 1 and R 2 are each independently an alkyl group having 1 to 3 carbon atoms, and R 3 is a hydrogen atom or a methyl group.

2. The one-part dental adhesive according to claim 1 , wherein the water (d) is contained in an amount of 1 to 50 weight %, and the polymerization initiator (e) is contained in an amount of 0.01 to 10 weight %.

3. The one-part dental adhesive according to claim 1 , wherein the water-soluble crosslinkable (meth)acrylic monomer (b-2) is at least one selected from the group consisting of a water-soluble bis(meth)acrylamide compound and 1,2-bis(3-methacryloyloxy-2-hydroxypropyloxy)ethane, the water-soluble bis(meth)acrylamide compound being represented by the following formula (2):

where:
X is a linear or branched aliphatic group that has 1 to 6 carbon atoms and in which at least one bond selected from the group consisting of —O—, —S—, —CO—O—, —CO—NH—,—O—CO—NH—, and —NH—CO—NH— may be included;
R 4 and R 5 are each independently a hydrogen atom or a linear or branched aliphatic group having 1 to 4 carbon atoms; and
R 6 and R 7 are each independently a hydrogen atom or a methyl group.

4. The one-part dental adhesive according to claim 1 , wherein the monofunctional (meth)acrylamide compound (b-1) is N,N-diethylaciylamide.

5. A one-part dental adhesive comprising:
polymerizable monomers;
water (d); and
a polymerization initiator (e),
wherein
the polymerizable monomers consist of 1 to 30 weight % of a phosphoric acid group-containing monofunctional (meth)acrylate compound (a), 10 to 50 weight % of a water-soluble polymerizable monomer (b), and 5 to 50 weight% of a hydrophobic crosslinkable (meth)acrylate compound (c),
the water-soluble polymerizable monomer (b) consists of a combination of a monofunctional (meth)acrylamide compound (b-1) and a water-soluble crosslinkable (meth)acrylic monomer (b-2),
a weight ratio between the monofunctional (meth)acrylamide compound (b-1) and the water-soluble crosslinkable (meth)acrylic monomer (b-2) is 10:1 to 1:5, and
the monofunctional (meth)acrylamide compound (b-1) is represented by the following formula (1):

where
R 1 and R 2 are each independently an alkyl group having 1 to 3 carbon atoms, and R 3 is a hydrogen atom or a methyl group.

6. The one-part dental adhesive according to claim 1 , wherein the monofunctional (meth)acrylamide compound (b-1) is N,N-dimethylacrylamide.

7. The one-part dental adhesive according to claim 1 , wherein the water-soluble crosslinkable (meth)acrylic monomer (b-2) is 1,3-bis(acrylamido)propane.

8. The one-part dental adhesive according to claim 1 , wherein the water-soluble crosslinkable (meth)acrylic monomer (b-2) is N,N′-methylenebisacrylamide.

9. The one-part dental adhesive according to claim 1 , wherein the water-soluble crosslinkable (meth)acrylic monomer (b-2) is 1,2-bis(acrylamido)ethane.

10. The one-part dental adhesive according to claim 1 , wherein the water-soluble crosslinkable (meth)acrylic monomer (b-2) is 1,6-bis(acrylamido)hexane.

11. The one-part dental adhesive according to claim 1 , wherein the water-soluble crosslinkable (meth)acrylic monomer (b-2) is 1,2-bis(3-methacryloyloxy-2-hydroxypropyloxy)ethane.

12. The one-part dental adhesive according to claim 1 , wherein the hydrophobic crosslinkable (meth)acrylate compound (c) is 2,2-bis[4-(3-(methacryloyoxy)-2-hydroxypropoxy)phenyl]propane.

13. The one-part dental adhesive according to claim 1 , wherein the hydrophobic crosslinkable (meth)acrylate compound (c) is [2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl)]dimethacrylate.

14. The one-part dental adhesive according to claim 1 , wherein the hydrophobic crosslinkable (meth)acrylate compound (c) is triethylene glycol dimethacrylate.

15. The one-part dental adhesive according to claim 1 , wherein the hydrophobic crosslinkable (meth)acrylate compound (c) is neopentyl glycol dimethacrylate.

Assignees

• Kuraray Noritake Dental Inc

Inventors

• Takei Mitsuru
• Nojiri Yamato

Classifications

• A61K6/818

  comprising zirconium oxide · CPC title

• A61K6/889 Primary

  Polycarboxylate cements; Glass ionomer cements · CPC title

• A61K6/75

  Apatite · CPC title

• A61K6/30

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

• A61K6/60

  comprising organic or organo-metallic additives · CPC title