Photocurable composition, cured product, and dental product

Patent metadata

Field	Value
Publication number	US-11866527-B2
Application number	US-202117912098-A
Country	US
Kind code	B2
Filing date	Mar 22, 2021
Priority date	Mar 27, 2020
Publication date	Jan 9, 2024
Grant date	Jan 9, 2024

Abstract

A photocurable composition includes a photopolymerizable component and a photopolymerization initiator. When a test piece with 39 mm length, 8 mm width, and 4 mm thickness, is produced by photofabrication under conditions in which the photocurable composition is irradiated with visible light having 405 nm wavelength at 12 mJ/cm2 irradiation dose to form a cured layer with 100 m thickness, the cured layer is stacked in a thickness direction thereof to form a rectangular fabrication product with 39 mm length, 8 mm width, and 4 mm thickness, and the fabrication product is irradiated with ultraviolet rays having 365 nm wavelength at 10 J/cm2 irradiation dose to produce the test piece, a total fracture work of the test piece measured in compliance with ISO20795-1:2008 is 1100 J/m2 or more.

First claim

The invention claimed is:

1. A photocurable composition comprising a photopolymerizable component and a photopolymerization initiator, wherein:
in a case in which a test piece P1 with a length of 39 mm, a width of 8 mm, and a thickness of 4 mm, is produced by photofabrication under conditions in which the photocurable composition is irradiated with visible light having a wavelength of 405 nm at an irradiation dose of 12 mJ/cm 2 to form a cured layer P1 with a thickness of 100 m, the cured layer P1 is stacked in a thickness direction thereof to form a rectangular fabrication product P1 with a length of 39 mm, a width of 8 mm, and a thickness of 4 mm, and the fabrication product P1 is irradiated with ultraviolet rays having a wavelength of 365 nm at an irradiation dose of 10 J/cm 2 to produce the test piece P1, a total fracture work of the test piece P1 measured in compliance with ISO20795-1:2008 is 1100 J/m 2 or more;
wherein the photopolymerizable component comprises:
a di(meth)acrylic monomer (A) having two (meth)acryloyloxy groups and two urethane bonds; and
an acrylic monomer (B) having one acryloyl group; and
wherein di(meth)acrylic monomer (A) comprises a compound represented by the following Formula (1),

wherein, in Formula (1), R 1 is a divalent chain hydrocarbon group, a divalent hydrocarbon group with an aromatic structure, or a divalent hydrocarbon group with an alicyclic structure: each of R 2 and R 3 is independently a divalent chain hydrocarbon group that may have a substituent; and each of R 4 and R 5 is independently a methyl group or a hydrogen atom.

2. The photocurable composition according to claim 1 , wherein:
in a case in which a test piece P2 with a length of 64 mm, a width of 10 mm, and a thickness of 3.3 mm, is produced by photofabrication under conditions in which the photocurable composition is irradiated with visible light having a wavelength of 405 nm at an irradiation dose of 12 mJ/cm 2 to form a cured layer P2 with a thickness of 100 m, the cured layer P2 is stacked in a thickness direction thereof to form a rectangular fabrication product P2 with a length of 64 mm, a width of 10 mm, and a thickness of 3.3 mm, and the fabrication product P2 is irradiated with ultraviolet rays having a wavelength of 365 nm at an irradiation dose of 10 J/cm 2 to produce the test piece P2, a flexural modulus of the test piece P2 measured in compliance with ISO20795-1:2008 is 2,500 MPa or less.

3. The photocurable composition according to claim 1 , wherein
in a case in which a test piece P2 with a length of 64 mm, a width of 10 mm, and a thickness of 3.3 mm, is produced by photofabrication under conditions in which the photocurable composition is irradiated with visible light having a wavelength of 405 nm at an irradiation dose of 12 mJ/cm 2 to form a cured layer P2 with a thickness of 100 m, the cured layer P2 is stacked in a thickness direction thereof to form a rectangular fabrication product P2 with a length of 64 mm, a width of 10 mm, and a thickness of 3.3 mm, and the fabrication product P2 is irradiated with ultraviolet rays having a wavelength of 365 nm at an irradiation dose of 10 J/cm 2 to produce the test piece P2, a flexural strength of the test piece P2 measured in compliance with ISO20795-1:2008 is 70 MPa or less.

4. The photocurable composition according to claim 1 , wherein a proportion of a number of acryloyl groups with respect to a total number of acryloyl groups and methacryloyl groups in the photocurable composition is 40% or more.

5. The photocurable composition according to claim 1 , wherein, in Formula (1):
R 1 is a divalent hydrocarbon group with an aromatic structure, having from 6 to 12 carbon atoms, or a divalent hydrocarbon group with an alicyclic structure, having from 6 to 12 carbon atoms; and
each of R 2 and R 3 is independently a divalent chain hydrocarbon group having from 2 to 6 carbon atoms and no substituent.

6. The photocurable composition according to claim 1 , wherein the acrylic monomer (B) comprises at least one of a compound represented by the following Formula (2) or a compound represented by the following Formula (3),

wherein, in Formula (2), R 6 is a monovalent organic group that may have a ring structure, and
wherein, in Formula (3), each of R 7 and R 8 is independently a hydrogen atom or a monovalent organic group that may have a ring structure, and R 7 and R 8 may form a ring by bonding with each other.

7. The photocurable composition according to claim 6 , wherein:
the acrylic monomer (B) comprises the compound represented by Formula (2); and
in Formula (2), R 6 is a monovalent organic group with a ring structure, having from 6 to 20 carbon atoms.

8. The photocurable composition according to claim 1 , wherein a weight-average molecular weight of the di(meth)acrylic monomer (A) is from 380 to 4,000.

9. The photocurable composition according to claim 1 , wherein a weight-average molecular weight of the acrylic monomer (B) is from 130 to 320.

10. The photocurable composition according to claim 1 , wherein a content of the di(meth)acrylic monomer (A) is from 200 parts by mass to 850 parts by mass with respect to 1000 parts by mass of a total content of (meth)acrylic monomer components comprised in the photocurable composition.

11. The photocurable composition according to claim 1 , wherein a total content of the di(meth)acrylic monomer (A) and the acrylic monomer (B) is 800 parts by mass or more with respect to 1000 parts by mass of a total content of (meth)acrylic monomer components comprised in the photocurable composition.

12. The photocurable composition according to claim 1 , having a viscosity of from 20 mPa·s to 5000 mPa·s, measured with an E-type viscometer under conditions of 25° C. and 50 rpm.

13. The photocurable composition according to claim 1 , which is a photocurable composition for photofabrication.

14. A cured product of the photocurable composition according to claim 1 .

15. A dental product comprising the cured product according to claim 14 .

16. The dental product according to claim 15 , which is a medical device used in an oral cavity.

17. The photocurable composition according to claim 3 , wherein the flexural strength of the test piece P2 measured in compliance with ISO20795-1:2008 is from 3 MPa to 42 MPa.

Assignees

• Mitsui Chemicals Inc

Inventors

• Sakamaki Toshikazu
• Kimura Mai
• Murai Hiroki
• Hayashi Takaaki
• Endo Suguru

Classifications

• C08F2/50 Primary

  with sensitising agents · CPC title

• A61C13/0019

  using three dimensional printing · CPC title

• A61K6/62

  Photochemical radical initiators · CPC title

• A61K6/887

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

• C08F220/1811

  C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate · CPC title