# US 10,117,809 B2 · Compositions for endodontic procedures

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- Number: US 10,117,809 B2
- Document ID: US10117809B2
- Status: Granted
- Kind: B2
- Application number: 15/139,959
- Filed: 2016-04-27
- Published: 2016-08-18
- Granted: 2018-11-06
- Earliest claimed: 2012-07-13
- Assignees: DENTSPLY SIRONA Inc.
- Applicants: DENTSPLY SIRONA, Inc.
- Inventors: Todd Berger; Kevin Wilkinson; Adam Baratz; Dan Ammon
- Web page: https://patentgrep.com/patent/US10117809B2

## CPC

- A61C 5/50: Implements for filling root canals; Methods or instruments for medication of tooth nerve channels
- A61K 6/54: Filling; Sealing
- A61K 6/77: Glass
- A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- A61K 6/896: Polyorganosilicon compounds
- C07F 7/0838: {Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21)}
- C08F 220/325: {containing glycidyl radical, e.g. glycidyl (meth)acrylate}
- C08F 230/02: containing phosphorus
- C08F 230/08: containing silicon
- A61C: DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE (non-driven toothbrushes A46B; {tongue scrapers A61B17/24;} preparations for dentistry A61K6/00; preparations for cleaning the teeth or mouth A61K8/00, A61Q11/00)
- 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)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

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

## Claims

### Claim 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):
R1—R2—W—Z—R3—R4 (I)
wherein
wherein
R1 and R4 are independently Hydrogen, NH2, 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;
R2 and R3 are independently a C1-10 alkyl group, NH2, 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;
R5, R6, R7, R8, R9, R10, R11, and R12 are independently Hydrogen, a C1-10 alkyl group, or a C1-10—R13 group such that R13 is independently NH2, 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 R5, R6, R7, R8, R9, R10, R11, R12, and R13 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.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 3)

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

### Claim 5 (depends on 4)

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.

### Claim 6 (depends on 1)

The composition of claim 1, wherein:
i) R1 and R4 are independently an epoxide, a succunic anhydride, or a succinimide group;
ii) R1 and R4 are independently NH2, OH, COOH, or SH group; or
iii) at least one of R1 and R4 is independently a phosphate, a sulfate, a sulfonate, a betaine, a carboxylic acid, an amino acid, a diacids, a bisphosphate, or a phosphatidylcholine group.

### Claim 7 (depends on 1)

The composition of claim 1, wherein:
i) R1 and R4 are independently an epoxide, a succunic anhydride, or a succinimide group; and
ii) at least one of R5, R6, R7, R8, R9, R10, R11, and R12 is independently the C1-10—R13 group such that R13 is independently the phosphate, the sulfate, the sulfonate, the betaine, the carboxylic acid, the amino acid, the diacids, the bisphosphate, or the phosphatidylcholine group.

### Claim 8 (depends on 1)

The composition of claim 1, wherein:
i) R1 and R4 are independently NH2, OH, COOH, or SH group; and
ii) at least one of R5, R6, R7, R8, R9, R10, R11, and R12 is independently the C1-10—R13 group such that R13 is independently the phosphate, the sulfate, the sulfonate, the betaine, the carboxylic acid, the amino acid, the diacids, the bisphosphate, or the phosphatidylcholine group.

### Claim 9 (depends on 1)

The composition of claim 1, wherein:
i) at least one of R1 and R4 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 R5, R6, R7, R8, R9, R10, R11, and R12 is independently the C1-10—R13 group such that R13 is independently the NH2, OH, COOH, SH, epoxide, succunic anhydride, or succinimide group, whereas NH2, OH, COOH, or SH group is not present when the epoxide, the succunic anhydride, or the succinimide group is present.

### Claim 10 (depends on 1)

The composition of claim 1, wherein R5, R6, R11, and R12 are independently a C1-10 alkyl group.

### Claim 11 (depends on 1)

The composition of claim 1, wherein
and
wherein
R1 and R4 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 R1 and R4 is not Hydrogen;
R2 and R3 are independently a C1-10 alkyl group; and
R5, R6, R7, R8, R9, R10, R11, and R12 are independently Hydrogen, a C1-10 alkyl group, or a C1-10—R13 group such that R13 is independently NH2, OH, COOH, SH, an epoxide, a succunic anhydride, or a succinimide group, whereas multiple groups of R7, R8, R9, R10, R11, R12, and R13 may be identical or different, provided at least two of R5, R6, R7, R8, R9, R10, R11, and R12 includes the C1-10—R13 group.

### Claim 12 (depends on 11)

The composition according to claim 11, wherein NH2, OH, COOH, or SH is not present when the epoxide, the succunic anhydride, or the succinimide group is present.

### Claim 13 (depends on 11)

The composition of claim 11, wherein at least two of R5, R6, R7, R8, R9, R10, R11, and R12 includes the C1-10—R13 group.

### Claim 14 (depends on 11)

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

### Claim 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):
R1—R2—W—Z—R3—R4 (IIa);
wherein
R1 and R4 are independently NH2, OH, COOH, or SH;
R2 and R3 are independently a C1-10 alkyl group;
R5, R6, R7, R8, R9, R10, R11 and R12 are independently Hydrogen, a C1-10 alkyl group, or a C1-10—R13 group such that R13 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 R5, R6, R7, R8, R9, R10, R11, R12, and R13 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):
R13—R14—W—Z—R15—R16 (IIb);
wherein
R13 and R16 are independently an epoxide, a succunic anhydride, or a succinimide group;
R14 and R15 are independently a C1-10 alkyl group;
R16, R17, R18, R19, R20, R21, R22, and R23 are independently Hydrogen, a C1-10 alkyl group, or a C1-10—R24 group such that R24 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 R16, R17, R18, R19, R20, R21, R22, R23, and R24 may be identical or different;
q is an integer from 1 to 1000, multiple groups of q may be identical or different;
r is an integer from 1 to 1000, multiple groups of r may be identical or different; and
s is an integer from 1 to 10, multiple groups of s may be identical or different.

### Claim 16 (depends on 15)

The composition of claim 15, wherein
i) at least one of R5, R6, R7, R8, R9, R10, R11, R12 includes the C1-10—R13 group; and/or
ii) at least one of R16, R17, R18, R19, R20, R21, R22, and R23 includes the C1-10—R24 group.

### Claim 17 (depends on 15)

The composition of claim 15, wherein
i) at least one of R7 and R8 includes the C1-10—R13 group; and/or
ii) at least one of R18 and R19 includes the C1-10—R24 group.

### Claim 18 (depends on 15)

The composition of claim 15, wherein x ranges from 1-50, y ranges from 25-250, and m is 1 and wherein q ranges from 1-50, r ranges from 25-250, and s is 1.

### Claim 19

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 (IIIa):
R1—R2—W—Z—R3—R4 (IIIa);
wherein
R1 and R4 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 R1 and R4 is not Hydrogen;
R2 and R3 are independently a substituted or unsubstituted C1-10 alkyl group;
R5, R6, R7, R8, R9, R10, R11 and R12 are independently Hydrogen, a C1-10 alkyl group, or a C1-10—R13 group such that R13 is independently NH2, OH, COOH, SH, whereas multiple groups of R7, R8, R9, R10, R11, R12, and R13 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 (IIIb):
R13—R14—W—Z—R15—R16 (IIIb);
wherein
R13 and R16 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 R1 and R4 is not Hydrogen;
R14 and R15 are independently a substituted or unsubstituted C1-10 alkyl group;
R16, R17, R18, R19, R20, R21, R22, and R23 are independently Hydrogen, a C1-10 alkyl group, or a C1-10—R24 group such that R24 is independently an epoxide, a succunic anhydride, or a succinimide group, whereas multiple groups of R16, R17, R18, R19, R20, R21, R22, R23, and R24 may be identical or different;
q is an integer from 1 to 1000, multiple groups of q may be identical or different;
r is an integer from 1 to 1000, multiple groups of r may be identical or different; and
s is an integer from 1 to 10, multiple groups of s may be identical or different.

### Claim 20 (depends on 19)

The composition of claim 19, wherein
i) at least one of R5, R6, R7, R8, R9, R10, R11, R12 includes the C1-10—R13 group; and/or
ii) at least one of R16, R17, R18, R19, R20, R21, R22, and R23 includes the C1-10—R24 group.

### Claim 21 (depends on 19)

The composition of claim 19, wherein x ranges from 1-50, y ranges from 25-250, and m is 1; and wherein q ranges from 1-50, r ranges from 25-250, and s is 1.

### Claim 22

An endodontic composite sealant composition for filling and sealing a root canal comprising an adhesion promoter, wherein adhesion promoter is characterized by the following formula (IV):
R1—W—Z—R2 (IV)
wherein
R1 and R2 are independently a substituted or unsubstituted C1-11alkyl group;
wherein
R3, R4, R5, R6, R7, R8, R9, and R10 are independently Hydrogen, a C1-10 alkyl group, or a C1-10—R11 group such that R11 is independently NH2, 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 R3, R4, R5, R6, R7, R8, R9, R10, and R11 may be identical or different; provided that at least one of R3, R4 R5, R6, R7, and R8 includes the C1-10—R11 group;
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.

### Claim 23 (depends on 22)

The composition according to claim 22, wherein NH2, OH, COOH, or SH is not present when the epoxide, the succunic anhydride, or the succinimide group is present.

### Claim 24 (depends on 22)

The composition of claim 22, wherein
and
wherein
R3, R4, R7, R8, R9, R10, and R11 include the C1-10 alkyl group;
x ranges from 1-50;
y ranges from 25-250; and
m is 1.

### Claim 25

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 (IVa):
R1—W—Z—R2 (IVa)
wherein
R1 and R2 are independently a substituted or unsubstituted C1-11 alkyl group;
wherein
R3, R4, R5, R6, R7, R8, R9, and R10 are independently Hydrogen, a C1-10 alkyl group, or a C1-10—R11 group such that R11 is independently NH2, OH, COOH, or SH; whereas multiple groups of R3, R4, R5, R6, R7, R8, R9, R10, and R11 may be identical or different; provided that at least one of R3, R4 R5, R6, R7, and R8 includes the C1-10—R11 group;
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 (IVb):
R12—W—Z—R13 (IVb)
wherein
R12 and R13 are independently a substituted or unsubstituted C1-11 alkyl group;
wherein
R14, R15, R16, R17, R18, R19, R20, and R21 are independently Hydrogen, a C1-10 alkyl group, or a C1-10—R22 group such that R22 is independently an epoxide, a succunic anhydride, or a succinimide group; whereas multiple groups of R14, R15, R16, R17, R18, R19, R20, R21, and R22 may be identical or different; provided that at least one of R14, R15, R16, R17, R18, and R19 includes the C1-10—R11 group;
q is an integer from 1 to 1000, multiple groups of x may be identical or different;
r is an integer from 1 to 1000, multiple groups of y may be identical or different; and
s is an integer from 1 to 10, multiple groups of m may be identical or different.

### Claim 26 (depends on 25)

The composition of claim 25, wherein
i) at least one of R5, R6, R7, and R8 includes the C1-10—R11 group; and
ii) at least one of R16, R17, R18, and R19 includes the C1-10—R22 group.

### Claim 27 (depends on 25)

The composition of claim 25, wherein x ranges from 1-50, y ranges from 25-250, and m is 1; and wherein q ranges from 1-50, r ranges from 25-250, and s is 1.

### Claim 28 (depends on 25)

The composition of claim 25, wherein
i) at least one of R5, R6, R7, and R8 is independently a C1-10—R23 group such that R23 is 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 R5, R6, R7, and R8 may be identical or different; and/or
ii) at least one of R16, R17, R18, and R19 is independently a C1-10—R24 group such that R24 is 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 R16, R17, R18, and R19 may be identical or different.

### Claim 29 (depends on 1)

The composition of claim 1, further comprising bioglass or a bioactive glass.

### Claim 30 (depends on 15)

The composition of claim 15, wherein the first component, the second component or both further include bioglass or a bioactive glass.

### Claim 31 (depends on 19)

The composition of claim 19, wherein the first component, the second component or both further include bioglass or a bioactive glass.

### Claim 32 (depends on 22)

The composition of claim 22, further comprising bioglass or a bioactive glass.

### Claim 33 (depends on 25)

The composition of claim 25, wherein the first component, the second component or both further include bioglass or a bioactive glass.