Photocurable composition, denture base, and plate denture

Patent metadata

Field	Value
Publication number	US-10562995-B2
Application number	US-201615765353-A
Country	US
Kind code	B2
Filing date	Oct 4, 2016
Priority date	Oct 8, 2015
Publication date	Feb 18, 2020
Grant date	Feb 18, 2020

Abstract

Provided is a photocurable composition including a monomer component including: a monomer (X) containing, within one molecule, two aromatic rings and two (meth)acryloyloxy groups, and having an Mw of from 400 to 580, and a monomer (H) containing, within one molecule, at least one of a hydroxyl group or a carboxy group, and a (meth)acryloyloxy group, and having an Mw of from 100 to 700; and a photopolymerization initiator. The composition has a functional group value (a) of from 0.5×10 −3 to 2.0×10 −3 mol/g.

Functional group value ( a )=( n H /M H )× P H   Formula (a)

wherein n H represents the total number of hydroxyl groups and carboxy groups contained in one molecule of the (meth)acrylic monomer (H); M H represents the Mw of the (meth)acrylic monomer (H); and P H represents the mass ratio of the (meth)acrylic monomer (H) with respect to the total amount of the (meth)acrylic monomer component.

First claim

The invention claimed is:

1. A photocurable composition for use in stereolithography, the photocurable composition comprising:
a (meth)acrylic monomer component comprising:
a (meth)acrylic monomer (X) that is at least one selected from di(meth)acrylic monomers not containing, within one molecule, a hydroxyl group or a carboxy group and containing, within one molecule, two aromatic rings and two (meth)acryloyloxy groups, and that has a weight average molecular weight of from 400 to 580, and
a (meth)acrylic monomer (H) that is at least one selected from (meth)acrylic monomers containing, within one molecule, at least one of a hydroxyl group or a carboxy group, and a (meth)acryloyloxy group, and that has a weight average molecular weight of from 100 to 700; and

a photopolymerization initiator,
wherein a functional group value (a) as defined by the following Formula (a) is from 0.50×10 −3 mol/g to 2.00×10 −3 mol/g:
functional group value ( a )=( n H /M H )× P H   Formula (a)

wherein, in Formula (a), n H represents a total number of hydroxyl groups and carboxy groups contained in one molecule of the (meth)acrylic monomer (H); M H represents the weight average molecular weight of the (meth)acrylic monomer (H); and P H represents a mass ratio of the (meth)acrylic monomer (H) with respect to a total amount of the (meth)acrylic monomer component, a content of the acrylic monomer (H) is 350 parts by mass or less with respect to 1,000 parts by mass of a total content of the (meth)acrylic monomer component.

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

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

wherein, in Formula (x-1), each of R 1x , R 2x , R 11x , and R 12x 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 di(meth)acrylic monomer constituting the (meth)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 , R 8x , R 11x , and R 12x independently represents a hydrogen atom or a methyl group; and each of mx and nx independently represents a number from 0 to 4, and mx and nx satisfy: 1≤(mx+nx)≤4.

6. The photocurable composition according to claim 1 , wherein the (meth)acrylic monomer component further comprises at least one of:
a (meth)acrylic monomer (A) that is at least one selected from di(meth)acrylic monomers not containing, within one molecule, a hydroxyl group, a carboxy group, or 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, a hydroxyl group, a carboxy group, or 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,
a (meth)acrylic monomer (C) that is at least one selected from di(meth)acrylic monomers not containing, within one molecule, a hydroxyl group, a carboxy group, an ether bond, or an aromatic ring 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, or
a (meth)acrylic monomer (D) that is at least one selected from (meth)acrylic monomers not containing, within one molecule, a hydroxyl group or a carboxy group and containing, within one molecule, an aromatic ring and one (meth)acryloyloxy group, and that has a weight average molecular weight of from 160 to 400.

7. The photocurable composition according to claim 6 , wherein:
in the case that the (meth)acrylic monomer (A) is contained, at least one di(meth)acrylic monomer constituting the (meth)acrylic monomer (A) is a compound represented by the following Formula (a-1);
in the case that the (meth)acrylic monomer (B) is contained, at least one (meth)acrylic monomer constituting the (meth)acrylic monomer (B) is a compound represented by the following Formula (b-1);
in the case that the (meth)acrylic monomer (C) is contained, at least one di(meth)acrylic monomer constituting the (meth)acrylic monomer (C) is a compound represented by the following Formula (c-1); and
in the case that the (meth)acrylic monomer (D) is contained, at least one (meth)acrylic monomer constituting the (meth)acrylic monomer (D) is a compound represented by the following Formula (d-1):

wherein,
in Formula (a-1), each of R 1a and R 2a independently represents a hydrogen atom or a methyl group; each R 3a 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;
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;
in Formula (c-1), each of R 1c and R 2c independently represents a hydrogen atom or a methyl group; and R 3c represents an alkylene group having from 1 to 9 carbon atoms; and
in Formula (d-1), R 1d represents a hydrogen atom or a methyl group; each R 2d independently represents a straight chain or branched chain alkylene group having from 1 to 5 carbon atoms; each R 3d independently represents a single bond, an ether bond (—O—), an ester bond (—O—(C═O)—), or —C 6 H 4 —O—; A 1d represents an aromatic ring; and nd represents a number from 1 to 2.

8. The photocurable composition according to claim 6 , wherein:
in the case that the (meth)acrylic monomer (A) is contained, at least one di(meth)acrylic monomer constituting the (meth)acrylic monomer (A) is a compound represented by the following Formula (a-2);
in the case that the (meth)acrylic monomer (B) is contained, at least one (meth)acrylic monomer constituting the (meth)acrylic monomer (B) is a compound represented by the following Formula (b-2);
in the case that the (meth)acrylic monomer (C) is contained, at least one di(meth)acrylic monomer constituting the (meth)acrylic monomer (C) is a compound represented by the following Formula (c-2); and
in the case that the (meth)acrylic monomer (D) is contained, at least one (meth)acrylic monomer constituting the (meth)acrylic monomer (D) is a compound represented by the following Formula (d-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;

Assignees

• Mitsui Chemicals Inc

Inventors

• Sakamaki Toshikazu
• Koura Takashi
• Kojima Kouya
• Shiode Hirohisa
• Kimura Mai

Classifications

• C08F222/10

  Esters · CPC title

• C08F220/26

  Esters containing oxygen in addition to the carboxy oxygen · CPC title

• G03F7/031

  Organic compounds not covered by group G03F7/029 · CPC title

• G03F7/0037

  Production of three-dimensional images · CPC title

• A61K6/887

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