# US 11,992,539 B2 · Curable dental compositions and uses thereof

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- Number: US 11,992,539 B2
- Document ID: US11992539B2
- Status: Granted
- Kind: B2
- Application number: 18/032,655
- Filed: 2021-11-03
- Published: 2023-12-21
- Granted: 2024-05-28
- Earliest claimed: 2020-11-25
- Assignees: Solventum Intellectual Properties Company
- Applicants: Solventum Intellectual Properties Company
- Inventors: Paul J. Homnick; Ahmed S. Abuelyaman
- Web page: https://patentgrep.com/patent/US11992539B2

## CPC

- A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- A61K 6/16: Refractive index
- A61K 6/17: Particle size
- A61K 6/71: Fillers
- C08F 222/1025: {of aromatic dialcohols}
- C08K 3/22: of metals
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

A curable dental composition includes a compound having structural formula (A) where X is an amine-, oxygen-, or sulfur-containing linkage; Y is an amine-, oxygen-, or sulfur-containing linkage; n is 1-15; m is 1-5; p is 1-5, with the proviso that when p is greater than 1, m is 1; each R1 is, independently, an alkyl or aryl group having 2 to 20 carbon atoms that is linear, branched, cyclic, or some combination thereof, and optionally includes one or more heteroatoms or unsaturated bonds; and each R2 is, independently, a hydrogen atom or CH3 The composition also includes filler. The filler is present in an amount of at least 25 wt.-%, based on the total weight of the curable dental composition.

## Claims

### Claim 1

A curable dental composition comprising:
a compound having structural formula (A):
where
X is an amine-, oxygen-, or sulfur -containing linkage;
Y is an amine-, oxygen-, or sulfur -containing linkage;
n is 1 -15;
m is 1 -5;
p is 1-5, with the proviso that when p is greater than 1, m is 1;
each R1 is, independently, an alkyl or aryl group having 2 to 20 carbon atoms that is linear, branched, cyclic, or some combination thereof, and optionally includes one or more heteroatoms or unsaturated bonds; and
each R2 is, independently, a hydrogen atom or CH3; and
filler, wherein filler is present in the curable dental composition in an amount of at least 25 wt.-%, based on the total weight of the curable dental composition.

### Claim 2 (depends on 1)

The curable dental composition of claim 1, wherein at least one R1 is selected from

### Claim 3 (depends on 1)

The curable dental composition of claim 1, wherein n is 1-10.

### Claim 4 (depends on 1)

The curable dental composition of claim 1, wherein m is 1-3.

### Claim 5 (depends on 1)

The curable dental composition of claim 1, wherein R1 has 4 to 7 carbon atoms.

### Claim 6 (depends on 1)

The curable dental composition of claim 1, wherein the compound having structural formula (A) is present in the curable composition in an amount of at least 5 wt.-%, based on the total weight of the curable dental composition.

### Claim 7 (depends on 1)

The curable dental composition of claim 1, wherein the refractive index of the compound having structural formula (A) is between 1.53 and 1.60 (nD20).

### Claim 8 (depends on 1)

The curable dental composition of claim 1, wherein the viscosity of compound (A) is no more than 3500 Pa*s at 25 degrees Celsius.

### Claim 9 (depends on 1)

The curable dental composition of claim 1, wherein the refractive index of a reaction product of the curable components of the curable composition inclusive of filler having a particle size of 100 nm or less differs from the refreactive index of the filler by less than 0.05.

### Claim 10 (depends on 1)

A method comprising producing a dental cement, a crown and bridge material, a dental filling material, a casting material, a cavity liner, a coating composition, a mill blank, an orthodontic devices, a sealant or combinations thereof using the curable composition of claim 1.

### Claim 11 (depends on 1)

An article comprising a cured composition, wherein the cured composition is the reaction product of the curable dental composition according to claim 1.