# US 11,718,744 B2 · Photo-curable resin compositions containing impact modifier for three dimensional printing and cured dental product made of the same

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- Number: US 11,718,744 B2
- Document ID: US11718744B2
- Status: Granted
- Kind: B2
- Application number: 17/214,603
- Filed: 2021-03-26
- Published: 2022-09-29
- Granted: 2023-08-08
- Earliest claimed: 2021-03-26
- Assignees: DENTCA, Inc.
- Applicants: DENTCA, Inc.
- Inventors: Jason Lee; Shuang Xiao; Jun Kyu Park
- Web page: https://patentgrep.com/patent/US11718744B2

## CPC

- A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C08L 33/14: of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- A61K 6/60: comprising organic or organo-metallic additives
- A61K 6/62: Photochemical radical initiators
- 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

A photocurable composition includes: about 45 to about 55 weight % of aromatic urethane di(meth)acrylate monomer having two urethane linkages and two acryloyloxy groups; about 20 to about 30 weight % of monofunctional (meth)acrylate monomer having acryloyl groups; about 8 to about 18 weight % of bifunctional (meth)acrylate monomer having ethoxy groups; about 5 to about 15 weight % of impact modifier having core-shell structure; about 0.2 to about 5.0 weight % of at least one kind of ultraviolet/visible (UV/Vis) light-photo-polymerization initiator; and at least one colorant.

## Claims

### Claim 1

A photocurable composition comprising:
about 45 to about 55 weight % of aromatic urethane di(meth)acrylate monomer having two urethane linkages and two acryloyloxy groups;
about 20 to about 30 weight % of monofunctional (meth)acrylate monomer having acryloyl groups;
about 8 to about 18 weight % of bifunctional (meth)acrylate monomer having ethoxy groups;
about 5 to about 15 weight % of impact modifier having core-shell structure;
about 0.2 to about 5.0 weight % of at least one kind of ultraviolet/visible (UV/Vis) light-photo-polymerization initiator; and
at least one colorant,
wherein the aromatic urethane di(meth)acrylate monomer having two urethane linkages and two acryloyloxy groups is a compound represented by the following formula (1):
wherein two substitutions on aromatic ring are either ortho, meta or para positions; R1 is a divalent chain hydrocarbon groups having 2 to 8 carbon atoms and do not have a substituent; and R2 independently represents a hydrogen atom or a methyl group.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the monofunctional (meth)acrylate monomer having acryloyl groups is represented by the following formula (2):
wherein R3 is a monovalent functional group having 6 to 20 carbon atoms and having an aromatic or alicyclic structure,
wherein the aromatic structure comprises benzylic groups with various substitutes,
wherein the alicyclic structure comprises cycloalkyl groups with various substitutes, and
wherein R4 independently represents a hydrogen atom or a methyl group.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the bifunctional (meth)acrylate monomer having ethoxy groups, having at least one of ethoxy groups as a middle block and (meth)acrylate groups at both ends, is represented by the following formula (3):
wherein R5 independently represents a hydrogen atom or a methyl group,
wherein n is repeat of ethoxy groups, and
wherein n is one of integers 1 to 6.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the core-shell structured impact modifier has 65 to 85 parts of a diolefin, 8 to 14 parts of an intermediate layer comprising a vinyl aromatic monomer, and 8 to 20 parts of outer shell comprising an alkyl methacrylate monomer.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the composition has a flexural strength of 50 to 100 MPa at 37° C. and total fracture work of 500-1100 J/m2 at 25° C. after the composition is cured.

### Claim 6 (depends on 1)

The composition of claim 1, wherein viscosity the composition is 1,000-5,000 cps at 25° C.