Compositions for endodontic procedures

Patent metadata

Field	Value
Publication number	US-10117809-B2
Application number	US-201615139959-A
Country	US
Kind code	B2
Filing date	Apr 27, 2016
Priority date	Jul 13, 2012
Publication date	Nov 6, 2018
Grant date	Nov 6, 2018

Abstract

An adhesion promoter for endodontic sealant compositions for filling and sealing a root canal.

First claim

The invention claimed is:

1. An endodontic composite sealant composition for filling and sealing a root canal comprising an adhesion promoter, wherein the adhesion promoter is characterized by the following formula (I):
R 1 —R 2 —W—Z—R 3 —R 4   (I)

wherein

wherein
R 1 and R 4 are independently Hydrogen, NH 2 , OH, COOH, SH, an epoxide, a succunic anhydride, a succinimide group, a phosphate, a sulfate, a sulfonate, a betaine, a carboxylic acid, an amino acid, a diacids, a bisphosphate, or a phosphatidylcholine group;
R 2 and R 3 are independently a C 1-10 alkyl group, NH 2 , OH, COOH, SH, an epoxide, a succunic anhydride, a succinimide group, a phosphate, a sulfate, a sulfonate, a betaine, a carboxylic acid, an amino acid, a diacids, a bisphosphate, or a phosphatidylcholine group;
R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 are independently Hydrogen, a C 1-10 alkyl group, or a C 1-10 —R 13 group such that R 13 is independently NH 2 , OH, COOH, SH, an epoxide, a succunic anhydride, a succinimide group, a phosphate, a sulfate, a sulfonate, a betaine, a carboxylic acid, an amino acid, a diacids, a bisphosphate, or a phosphatidylcholine group, whereas multiple groups of R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 may be identical or different; and
x is an integer from 1 to 1000, multiple groups of x may be identical or different;
y is an integer from 1 to 1000, multiple groups of y may be identical or different; and
m is an integer from 1 to 1000, multiple groups of m may be identical or different.

2. The composition of claim 1 , wherein a portion of the adhesion promoter includes a ring-opening functionality, a reactive-cyclic functionality, a free radical functionality, or any combination thereof.

3. The composition of claim 1 , wherein the adhesion promoter includes a dentin binding functionality.

4. The composition of claim 3 , wherein the dentin binding functionality includes a negative charge, a positive charge, an amphoteric charge, or a zwitterionic charge.

5. The composition of claim 4 , wherein the negative or positive charge comprises carboxylic acid groups, sulfate groups, amine groups, phosphate groups, quaternary ammonium groups and sulfonate, betaine, phosphatidylcholine groups.

6. The composition of claim 1 , wherein:
i) R 1 and R 4 are independently an epoxide, a succunic anhydride, or a succinimide group;
ii) R 1 and R 4 are independently NH 2 , OH, COOH, or SH group; or
iii) at least one of R 1 and R 4 is independently a phosphate, a sulfate, a sulfonate, a betaine, a carboxylic acid, an amino acid, a diacids, a bisphosphate, or a phosphatidylcholine group.

7. The composition of claim 1 , wherein:
i) R 1 and R 4 are independently an epoxide, a succunic anhydride, or a succinimide group; and
ii) at least one of R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 is independently the C 1-10 —R 13 group such that R 13 is independently the phosphate, the sulfate, the sulfonate, the betaine, the carboxylic acid, the amino acid, the diacids, the bisphosphate, or the phosphatidylcholine group.

8. The composition of claim 1 , wherein:
i) R 1 and R 4 are independently NH 2 , OH, COOH, or SH group; and
ii) at least one of R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 is independently the C 1-10 —R 13 group such that R 13 is independently the phosphate, the sulfate, the sulfonate, the betaine, the carboxylic acid, the amino acid, the diacids, the bisphosphate, or the phosphatidylcholine group.

9. The composition of claim 1 , wherein:
i) at least one of R 1 and R 4 is independently a phosphate, a sulfate, a sulfonate, a betaine, a carboxylic acid, an amino acid, a diacids, a bisphosphate, or a phosphatidylcholine group; and
ii) at least one of R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 is independently the C 1-10 —R 13 group such that R 13 is independently the NH 2 , OH, COOH, SH, epoxide, succunic anhydride, or succinimide group, whereas NH 2 , OH, COOH, or SH group is not present when the epoxide, the succunic anhydride, or the succinimide group is present.

10. The composition of claim 1 , wherein R 5 , R 6 , R 11 , and R 12 are independently a C 1-10 alkyl group.

11. The composition of claim 1 , wherein

and
wherein
R 1 and R 4 are independently Hydrogen, a phosphate, a sulfate, a sulfonate, a betaine, a carboxylic acid, an amino acid, a diacids, a bisphosphate, or a phosphatidylcholine group, provided at least one of R 1 and R 4 is not Hydrogen;
R 2 and R 3 are independently a C 1-10 alkyl group; and
R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 are independently Hydrogen, a C 1-10 alkyl group, or a C 1-10 —R 13 group such that R 13 is independently NH 2 , OH, COOH, SH, an epoxide, a succunic anhydride, or a succinimide group, whereas multiple groups of R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 may be identical or different, provided at least two of R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 includes the C 1-10 —R 13 group.

12. The composition according to claim 11 , wherein NH 2 , OH, COOH, or SH is not present when the epoxide, the succunic anhydride, or the succinimide group is present.

13. The composition of claim 11 , wherein at least two of R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 includes the C 1-10 —R 13 group.

14. The composition of claim 11 , wherein x ranges from 1-50, y ranges from 25-250, and m is 1.

15. An endodontic composite sealant composition for filling and sealing a root canal comprising an adhesion promoter, wherein the adhesion promoter includes a first component and a second component,
a) the first component is characterized by the following formula (IIa):
R 1 —R 2 —W—Z—R 3 —R 4   (IIa);

wherein
R 1 and R 4 are independently NH 2 , OH, COOH, or SH;
R 2 and R 3 are independently a C 1-10 alkyl group;

R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are independently Hydrogen, a C 1-10 alkyl group, or a C 1-10 —R 13 group such that R 13 is independently a phosphate, a sulfate, a sulfonate, a betaine, a carboxylic acid, an amino acid, a diacids, a bisphosphate, or a phosphatidylcholine group, whereas multiple groups of R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R 13 may be identical or different;
x is an integer from 1 to 1000, multiple groups of x may be identical or different;
y is an integer from 1 to 1000, multiple groups of y may be identical or different; and
m is an integer from 1 to 10, multiple groups of m may be identical or different; and

b) the second component is characterized by the following formula (IIb):
R 13 —R 14 —W—Z—R 15 —R 16   (IIb);

wherein
R 13 and R 16 are independently an epoxide, a succunic anhydride, or a succinimide group;
R 14 and R 15 are independently a C 1-10 alkyl group;

R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , and R 23 are independently Hydrogen, a C 1-10 alkyl group, or a C 1-10 —R 24 group such that R 24 is independently a phosphate, a sulfate, a

Assignees

• Dentsply Sirona Inc
• Dentsply Sirona Inc

Inventors

• Berger Todd
• Wilkinson Kevin
• Baratz Adam
• Ammon Dan

Classifications

• A61C5/50 Primary

  Implements for filling root canals; Methods or instruments for medication of tooth nerve channels · CPC title

• A61K6/77

  Glass · CPC title

• A61K6/887

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

• A61K6/896

  Polyorganosilicon compounds · CPC title

• A61K6/54

  Filling; Sealing · CPC title