Photocurable composition, denture base, and plate denture

Patent metadata

Field	Value
Publication number	US-10709530-B2
Application number	US-201615547217-A
Country	US
Kind code	B2
Filing date	Feb 1, 2016
Priority date	Feb 3, 2015
Publication date	Jul 14, 2020
Grant date	Jul 14, 2020

Abstract

The present invention provides a photocurable composition which is used for the production by stereolithography of a dental prosthesis or the like. This photocurable composition contains a (meth)acrylic monomer component and a photopolymerization initiator; and the (meth)acrylic monomer component contains: an acrylic monomer (X) containing, within one molecule, two aromatic rings and two acryloyloxy groups, and having a Mw of from 400 to 580; and at least one of: a (meth)acrylic monomer (A) containing, within one molecule, one or more ether bonds and two (meth)acryloyloxy groups, and having a Mw of from 200 to 400; a (meth)acrylic monomer (B) not containing, within one molecule, a ring structure other than an aromatic ring and one (meth)acryloyloxy group, and having a Mw of from 130 to 240; or a (meth)acrylic monomer (C) containing, within one molecule, a hydrocarbon skeleton and two (meth)acryloyloxy groups, and having a Mw of from 190 to 280.

First claim

The invention claimed is:

1. A photocurable composition that is used for production by stereolithography of a dental prosthesis, a medical device for intraoral use, or a tooth and/or jaw model, the photocurable composition comprising:
a (meth)acrylic monomer component and a photopolymerization initiator;
wherein the (meth)acrylic monomer component comprises:
an acrylic monomer (X) that is at least one selected from diacrylic monomers containing, within one molecule, two aromatic rings and two acryloyloxy groups, and that has a weight average molecular weight of from 400 to 580; and
at least one selected from the group consisting of:
a (meth)acrylic monomer (A) that is at least one selected from di(meth)acrylic monomers not containing, within one molecule, an aromatic ring and containing, within one molecule, one or more ether bonds and two (meth)acryloyloxy groups, and that has a weight average molecular weight of from 200 to 400;
a (meth)acrylic monomer (B) that is at least one selected from (meth)acrylic monomers not containing, within one molecule, an aromatic ring and containing, within one molecule, a ring structure other than an aromatic ring and one (meth)acryloyloxy group, and that has a weight average molecular weight of from 130 to 240; and
a (meth)acrylic monomer (C) that is at least one selected from di(meth)acrylic monomers not containing, within one molecule, an aromatic ring or an ether bond and containing, within one molecule, a hydrocarbon skeleton and two (meth)acryloyloxy groups, and that has a weight average molecular weight of from 190 to 280, and

wherein the photopolymerization initiator is at least one selected from alkylphenone compounds or acylphosphine oxide compounds.

2. The photocurable composition according to claim 1 , wherein at least one of the diacrylic monomers constituting the acrylic monomer (X) contains an ether bond within one molecule.

3. The photocurable composition according to claim 1 , wherein at least one of the diacrylic monomers constituting the acrylic monomer (X) contains from one to four ether bonds within one molecule.

4. The photocurable composition according to claim 1 , wherein at least one of the diacrylic monomers constituting the acrylic monomer (X) is a compound represented by the following Formula (x-1):

wherein, in Formula (x-1), each of R 1x and R 2x independently represents a hydrogen atom or a methyl group; each of R 3x and R 4x independently represents a straight chain or branched chain alkylene group having from 2 to 4 carbon atoms; and each of mx and nx independently represents a number from 0 to 4, and wherein mx and nx satisfy: 1≤(mx+nx)≤4.

5. The photocurable composition according to claim 1 , wherein at least one of the diacrylic monomers constituting the acrylic monomer (X) is a compound represented by the following Formula (x-2):

wherein, in Formula (x-2), each of R 5x , R 6x , R 7x , and R 8x independently represents a hydrogen atom or a methyl group; and each of mx and nx independently represents a number from 0 to 4, and wherein mx and nx satisfy: 1≤(mx+nx)≤4.

6. The photocurable composition according to claim 1 , wherein at least one of the di(meth)acrylic monomers constituting the (meth)acrylic monomer (A) is a compound represented by the following Formula (a-1):

wherein, in Formula (a-1), each of R 1a and R 2a independently represents a hydrogen atom or a methyl group; each lea independently represents a straight chain or branched chain alkylene group having from 2 to 4 carbon atoms; and p represents a number from 2 to 4.

7. The photocurable composition according to claim 1 , wherein at least one of the di(meth)acrylic monomers constituting the (meth)acrylic monomer (A) is a compound represented by the following Formula (a-2):

wherein, in Formula (a-2), each of R 1a , R 2a , R 4a , R 5a , R 6a , and R 7a independently represents a hydrogen atom or a methyl group; and each of p, q, and r independently represents 0 or 1, and wherein p, q, and r satisfy: p+q+r≥2.

8. The photocurable composition according to claim 1 , wherein at least one of the (meth)acrylic monomers constituting the (meth)acrylic monomer (B) is a compound represented by the following Formula (b-1):

wherein, in Formula (b-1), R 1b represents a hydrogen atom or a methyl group; R 2b represents a single bond or a methylene group; and A 1 represents a ring structure other than an aromatic ring.

9. The photocurable composition according to claim 1 , wherein at least one of the (meth)acrylic monomers constituting the (meth)acrylic monomer (B) is a compound represented by the following Formula (b-2):

wherein, in Formula (b-2), R 1b represents a hydrogen atom or a methyl group; R 2b represents a single bond or a methylene group; and A 2 represents a ring structure containing a dicyclopentenyl skeleton, a dicyclopentanyl skeleton, a cyclohexane skeleton, a tetrahydrofuran skeleton, a morpholine skeleton, an isobornyl skeleton, a norbornyl skeleton, a dioxolane skeleton, or a dioxane skeleton.

10. The photocurable composition according to claim 1 , wherein at least one of the di(meth)acrylic monomers constituting the (meth)acrylic monomer (C) is a compound represented by the following Formula (c-1):

wherein, in Formula (c-1), each of R 1c and R 2c independently represents a hydrogen atom or a methyl group; and R 3′ represents an alkylene group having from 1 to 9 carbon atoms.

11. The photocurable composition according to claim 1 , wherein at least one of the di(meth)acrylic monomers constituting the (meth)acrylic monomer (C) is a compound represented by the following Formula (c-2):

wherein, in Formula (c-2), each of R 1c and R 2c independently represents a hydrogen atom or a methyl group; each of R 4c and R 5c independently represents a hydrogen atom or a methyl group; and nc represents a number from 1 to 9, and wherein an alkylene group represented by —(CR 4c R 5c ) nc — has from 1 to 9 carbon atoms.

12. The photocurable composition according to claim 1 , wherein a content of the acrylic monomer (X) is from 550 parts by mass to 800 parts by mass with respect to 1,000 parts by mass of a total content of the (meth)acrylic monomer component.

13. The photocurable composition according to claim 1 , wherein a content of the (meth)acrylic monomer (A) is from 100 parts by mass to 450 parts by mass with respect to 1,000 parts by mass of a total content of the (meth)acrylic monomer component.

14. The photocurable composition according to claim 1 , wherein a content of the (meth)acrylic monomer (B) is from 100 parts by mass to 450 parts by mass with respect to 1,000 parts by mass of a total content of the (meth)acrylic monomer component.

15. The photocurable composition according to claim 1 ,

Assignees

• Mitsui Chemicals Inc

Inventors

• Gomi Toshikazu
• Koura Takashi
• Shiode Hirohisa
• Kimura Mai

Classifications

• A61K6/887 Primary

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

• A61C13/0013

  using stereolithographic techniques · CPC title

• A61K6/00

  Preparations for dentistry · CPC title

• A61C13/1003

  by embedding in base material · CPC title

• A61C13/01 Primary

  Palates or other bases or supports for the artificial teeth; Making same · CPC title