# US 11,304,879 B2 · Adhesive composition for dental use

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- Number: US 11,304,879 B2
- Document ID: US11304879B2
- Status: Granted
- Kind: B2
- Application number: 17/048,799
- Filed: 2019-04-19
- Published: 2021-05-20
- Granted: 2022-04-19
- Earliest claimed: 2018-04-20
- Assignees: Kuraray Noritake Dental Inc.
- Applicants: Kuraray Noritake Dental Inc.
- Inventors: Yamato Nojiri; Naoki Nishigaki; Mitsunobu Kawashima
- Web page: https://patentgrep.com/patent/US11304879B2

## CPC

- A61K 6/30: Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
- A61K 6/62: Photochemical radical initiators
- C08L 43/02: Homopolymers or copolymers of monomers containing phosphorus
- C08L 2203/02: for biomedical use
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The present invention provides a dental adhesive composition that, even after photocuring with a high-output LED irradiator, shows high bond strength not only for dentin untreated by phosphoric acid etching but also for dentin treated by phosphoric acid etching. The present invention relates to a dental adhesive composition comprising a phosphoric acid group-containing polymerizable monomer (A), the phosphoric acid group-containing polymerizable monomer (A) comprising: a dihydrogen phosphate monoester group-containing polymerizable monomer (A-1) represented by general formula (1); a hydrogen phosphate diester group-containing polymerizable monomer (A-2) represented by general formula (2); and a phosphoric acid tetraester group-containing polymerizable monomer (A-3) represented by general formula (3).

## Claims

### Claim 1

A dental adhesive composition, comprising:
a phosphoric acid group-containing polymerizable monomer,
wherein the phosphoric acid group-containing polymerizable monomer comprises:
a dihydrogen phosphate monoester group-containing polymerizable monomer represented by formula (1);
a hydrogen phosphate diester group-containing polymerizable monomer represented by formula (2); and
a phosphoric acid tetraester group-containing polymerizable monomer represented by formula (3),
where R1, R2, R3, R4, R5, R6, and R7 each independently represent a hydrogen atom or a methyl group, and X1, X2, X3, X4, X5, X6, and X7 each independently represent a linear or branched hydrocarbon group having 8 to 16 carbon atoms, wherein the hydrocarbon group optionally has a hydrocarbon chain with one or more groups selected from the group consisting of an oxy group, a sulfide group, and a phenylene group.

### Claim 2 (depends on 1)

The dental adhesive composition according to claim 1, wherein the dental adhesive composition comprises a polymerizable monomer that is copolymerizable with the phosphoric acid group-containing polymerizable monomer.

### Claim 3 (depends on 2)

The dental adhesive composition according to claim 2, wherein the polymerizable monomer comprises at least one selected from the group consisting of a hydrophobic polymerizable monomer having no acidic group, and a hydrophilic polymerizable monomer having no acidic group.

### Claim 4 (depends on 1)

The dental adhesive composition according to claim 1, wherein the dental adhesive composition further comprises a polymerization initiator.

### Claim 5 (depends on 4)

The dental adhesive composition according to claim 4, wherein the polymerization initiator comprises a photopolymerization initiator.

### Claim 6 (depends on 1)

The dental adhesive composition according to claim 1, wherein R1, R2, R3, R4, R5, R6, and R7 are all the same, and X1, X2, X3, X4, X5, X6, and X7 are all the same.

### Claim 7 (depends on 1)

The dental adhesive composition according to claim 1, wherein the dental adhesive composition comprises from 0.1 to 30.0 parts by mass of the hydrogen phosphate diester group-containing polymerizable monomer and from 0.05 to 5.0 parts by mass of the phosphoric acid tetraester group-containing polymerizable monomer relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer.