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# c12) United States Patent 

# Matsushige et al. 

# (54) DENTAL ADHESIVE COMPOSITION 

(75) Inventors: Koji Matsushige, Tokyo (JP); Qian Cui, Tokyo (JP); Ayumi Dodomi, Tokyo (JP) 

(73) Assignee: Tokuyama Dental Corporation, Tokyo (JP) 

( * ) Notice: Subject to any disclaimer, the term ofthis patent is extended or adjusted under 35 U.S.C. 154(b) by 38 days. 

(21) Appl. No.: 13/511,952 

(22) PCT Filed: Dec. 2, 2010 

(86) PCT No.: PCT I JP2010/071597 § 371 (c)(l), (2), ( 4) Date: May 24, 2012 

(87) PCT Pub. No.: WO2011/068164 

PCT Pub. Date: Jun. 9, 2011 

## (65) Prior Publication Data 

US 2012/0238658 Al Sep. 20, 2012 

## (30) Foreign Application Priority Data 

Dec. 4, 2009 (JP) ................................. 2009-276046 

(51) Int. Cl. A61K6/083 A61K6/00 (2006.01) (2006.01) 

(52) U.S. Cl. CPC .................................... A61K 6/0023 (2013.01) USPC ........... 523/116; 523/115; 523/113; 523/118; 523/28 

(58) Field of Classification Search None See application file for complete search history. 

## (56) References Cited 

<img src='content_image/924668.jpg'>

## U.S. PATENT DOCUMENTS 

<img src='content_image/924684.jpg'>

# (IO) Patent No.: US 8,815,974 B2 

# (45) Date of Patent: Aug. 26, 2014 

## FOREIGN PATENT DOCUMENTS 

<img src='content_image/924669.jpg'>

International Search Report dated Jan. 18, 2011. 

Extended European Search Report dated Dec. 12, 2013 filed in cor› responding European patent application No. 10834614.9. 

* cited by examiner 

Primary Examiner - James J Seidleck 

Assistant Examiner - Peter A Salamon 

(74) Attorney, Agent, or Firm - Rankin, Hill & Clark LLP 

## (57) ABSTRACT 

[Problems] To provide a liquid dental adhesive composition which contains a phosphoric acid-type compound having a hydrogenphosphoric diester group as an acidic group-con› taining polymerizable monomer and, further, contains poly› valent metal ions, effectively preventing not only the gelation but also the formation of precipitates (cloudiness) during the storage. 

[Means for Solution] A dental adhesive composition which is acidic and contains an acidic group-containing polymerizable monomer (A), polyvalent metal ions (B), water (C), a water› soluble organic solvent (D) and fluoride ions (E), wherein at least 35% by mole of the acidic group-containing polymer› izable monomer (A) is a phosphoric acid-type compound having a hydrogenphosphoric di ester group, and the contents of the fluoride ions (E) and the polyvalent metal ions (B) are so set that a valence number ratio (RF) defined by the follow› ing formula (1): 

<img src='content_image/924683.jpg'>

wherein VF is a valence number of the fluoride ions (E) contained in the composition, and TV Pis a total valence number of the polyvalent metal ions (B) contained in the composition, satisfies a range of0.2 to 2.0. 

US008815974B2 

## OTHER PUBLICATIONS 

## 13 Claims, No Drawings 

