Photocurable composition, three-dimensional modeling product, and dental product

Patent metadata

Field	Value
Publication number	US-12371586-B2
Application number	US-202118004185-A
Country	US
Kind code	B2
Filing date	Jul 6, 2021
Priority date	Jul 7, 2020
Publication date	Jul 29, 2025
Grant date	Jul 29, 2025

Abstract

A photocurable composition, wherein: in a case in which a rectangular sheet-like test piece P 1 with a length of 40 mm, a width of 10 mm, and a thickness of 0.5 mm is produced by photomodeling under specific conditions, and a storage modulus is measured for the thus produced test piece P 1 by dynamic viscoelastic measurement with a measurement frequency of 1 Hz while increasing a temperature in a range of from 25° C. to 300° C. at a rate of 3° C./min, the storage modulus at 135° C. is 3.0×10 8 Pa 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 rectangular sheet-like test piece P1 with a length of 40 mm, a width of 10 mm, and a thickness of 0.5 mm is produced by photomodeling under conditions in which the photocurable composition is irradiated with visible light having a wavelength of 405 nm at an irradiation dose of 11 mJ/cm 2 to form a cured layer P1 with a thickness of 50 μm, the cured layer P1 is stacked in a thickness direction thereof to form a rectangular sheet-like modeling product P1 with a length of 40 mm, a width of 10 mm, and a thickness of 0.5 mm, and the modeling product P1 is irradiated with ultraviolet rays having a wavelength of 365 nm at an irradiation dose of 3 J/cm 2 to produce the test piece P1, and a storage modulus is measured for the thus produced test piece P1 by dynamic viscoelastic measurement with a measurement frequency of 1 Hz while increasing a temperature in a range of from 25° C. to 300° C. at a rate of 3° C./min, the storage modulus at 135° C. is 3.0×10 8 Pa or more;
in a case in which

a distance between an oxygen atom forming an oxy group in one of (meth)acryloyloxy groups and an oxygen atom forming an oxy group in another of (meth)acryloyloxy groups in a di(meth)acrylic monomer is determined as d1,
a di(meth)acrylic monomer which comprises two (meth)acryloyloxy groups and a cyclic structure, and has the d1 of 15.0 Å or more is determined as a di(meth)acrylic monomer (A), and a di(meth)acrylic monomer which comprises two (meth)acryloyloxy groups, and has the d1 of less than 15.0 Å is determined as a di(meth)acrylic monomer (B),
the photopolymerizable component comprises,

two kinds of the di(meth)acrylic monomer (A) that are different in the d1, or the di(meth)acrylic monomer (A), and at least one of a mono(meth)acrylic monomer (D), which comprises one (meth)acryloyloxy group and at least one of a branched structure or a cyclic structure, or the di(meth)acrylic monomer (B);
and wherein,
a content of the di(meth)acrylic monomer (A) is 75% by mass or more, with respect to a total amount of all of (meth)acrylic monomers contained in the photocurable composition.

2. The photocurable composition according to claim 1 , wherein the storage modulus at 135° C. is 3.5×10 9 Pa or less.

3. A photocurable composition, comprising a photopolymerizable component and a photopolymerization initiator, wherein:
in a case in which a rectangular sheet-like test piece P1 with a length of 40 mm, a width of 10 mm, and a thickness of 0.5 mm is produced by photomodeling under conditions in which the photocurable composition is irradiated with visible light having a wavelength of 405 nm at an irradiation dose of 11 mJ/cm 2 to form a cured layer P1 with a thickness of 50 μm, the cured layer P1 is stacked in a thickness direction thereof to form a rectangular sheetlike modeling product P1 with a length of 40 mm, a width of 10 mm, and a thickness of 0.5 mm, and the modeling product P1 is irradiated with ultraviolet rays having a wavelength of 365 nm at an irradiation dose of 3 J/cm 2 to produce the test piece P1, and a storage modulus is measured for the thus produced test piece P1 by dynamic viscoelastic measurement with a measurement frequency of 1 Hz while increasing a temperature in a range of from 25° C. to 300° C. at a rate of 3° C./min, the storage modulus at 135° C. is 3.0×10 8 Pa or more;
in a case in which

a distance between an oxygen atom forming an oxy group in one of (meth)acryloyloxy groups and an oxygen atom forming an oxy group in another of (meth)acryloyloxy groups in a di(meth)acrylic monomer is determined as d1,
a di(meth)acrylic monomer which comprises two (meth)acryloyloxy groups and a cyclic structure, and has the d1 of 17.0 Å or more is determined as a di(meth)acrylic monomer (X), and a di(meth)acrylic monomer which comprises two (meth)acryloyloxy groups and a cyclic structure, and has the d1 of 15.0 Å or more and less than 17.0 Å is determined as a di(meth)acrylic monomer (Y),
the photopolymerizable component comprises the di(meth)acrylic monomer (X) and the di(meth)acrylic monomer (Y);
and wherein,
a total content of the di(meth)acrylic monomer (X) and the di(meth)acrylic monomer (Y) is 80% by mass or more with respect to a total amount of all of (meth)acrylic monomers contained in the photocurable composition.

4. The photocurable composition according to claim 3 , wherein a content of the di(meth)acrylic monomer (X) is from 50% by mass to 90% by mass with respect to a total amount of (meth)acrylic monomer components.

5. The photocurable composition according to claim 3 , wherein a content of the di(meth)acrylic monomer (Y) is from 10% by mass to 50% by mass with respect to a total amount of (meth)acrylic monomer components.

6. The photocurable composition according to claim 1 , having a viscosity, which is measured by an E-type viscometer under conditions of 25° C. and 50 rpm, of from 5 mPa's to 6,000 mPa·s.

7. The photocurable composition according to claim 1 , which is a photocurable composition for photomodeling.

8. The photocurable composition according to claim 1 , which is used for production of a dental product by photomodeling.

9. A three-dimensional modeling product, which is a cured product of the photocurable composition according to claim 1 .

10. A dental product, comprising the three-dimensional modeling product according to claim 9 .

11. The dental product according to claim 10 , which is a dental surgical guide, a dental tray, a mouthpiece, or a dental model.

Assignees

• Mitsui Chemicals Inc

Inventors

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

Classifications

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• A61C13/34

  Making or working of models, e.g. preliminary castings, trial dentures; Dowel pins [4] · CPC title

• C08F222/1025

  of aromatic dialcohols · CPC title

• C08F222/104

  of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate · CPC title

• C08F222/103

  of trialcohols, e.g. trimethylolpropane tri(meth)acrylate · CPC title