CURABLE RESIN COMPOSITION AND MANUFACTURING METHOD OF THREE-DIMENSIONAL OBJECT USING THE SAME

• US 20190315979A1
• Filed: 04/08/2019
• Published: 10/17/2019
• Est. Priority Date: 04/16/2018
• Status: Active Grant

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Hiratani, Takayuki, Wada, Kyohei
• Granted Patent: US 11,613,661 B2
• Time in Patent Office: Days
• CPC Class Codes: B29C 64/291 for operating globally, e.g. together with selectively applied activators or inhibitors
• CPC Class Codes: B29K 2009/00 Use of rubber derived from conjugated dienes, as moulding material
• CPC Class Codes: B29K 2033/12 Polymers of methacrylic acid esters, e.g. PMMA, i.e. polymethylmethacrylate
• CPC Class Codes: B29K 2063/00 Use of EP, i.e. epoxy resins or derivatives thereof, as moulding material
• CPC Class Codes: B29K 2071/00 Use of polyethers , e.g. PEEK, i.e. polyether-etherketone or PEK, i.e. polyetherketone or derivatives thereof, as moulding material
• CPC Class Codes: B33Y 10/00 Processes of additive manufacturing
• CPC Class Codes: B33Y 70/00 Materials specially adapted for additive manufacturing
• CPC Class Codes: C09D 11/101 Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
• CPC Class Codes: C09D 11/102 containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
• CPC Class Codes: C09D 11/106 containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds

Abstract

A curable resin composition includes: an oxetane compound (A) having one oxetanyl group as a cationic polymerizable reactive group and at least one hydroxyl group; a cationic polymerizable compound (B) which is a cationic polymerizable compound other than the oxetane compound (A) and has two or more cationic polymerization reactive groups; a rubber particle (C); and a curing agent (D), wherein the oxetane compound (A) is contained at 30 parts by mass or more and 60 parts by mass or less, based on 100 parts by mass of total mass of the oxetane compound (A) and the cationic polymerizable compound (B), and the rubber particle (C) has a group capable of reacting with the oxetane compound (A) or the cationic polymerizable compound (B) on a surface of the rubber particle (C).

Claims

1. A curable resin composition comprising:

an oxetane compound (A) having one oxetanyl group as a cationic polymerizable reactive group and at least one hydroxyl group;

a cationic polymerizable compound (B) which is a cationic polymerizable compound other than the oxetane compound (A) and has two or more cationic polymerization reactive groups;

a rubber particle (C); and

a curing agent (D),

wherein the oxetane compound (A) is contained at 30 parts by mass or more and 60 parts by mass or less, based on 100 parts by mass of total mass of the oxetane compound (A) and the cationic polymerizable compound (B), and

the rubber particle (C) has a group capable of reacting with the oxetane compound (A) or the cationic polymerizable compound (B) on a surface of the rubber particle (C).

2. The curable resin composition according to claim 1, wherein the group capable of reacting with the oxetane compound (A) or the cationic polymerizable compound (B) is at least one group selected from the group consisting of a glycidyl group, an oxetanyl group, a hydroxyl group, and a carboxyl group.

3. The curable resin composition according to claim 2, wherein a resin selected from the group consisting of a (meth)acrylic acid ester-based copolymer, a copolymer of (meth)acrylic acid ester with glycidyl (meth)acrylate, and a copolymer of (meth)acrylic acid ester, glycidyl (meth)acrylate, and styrene, is provided on at least a portion of a surface of the rubber particle (C).

4. The curable resin composition according to claim 1, wherein the cationic polymerizable compound (B) has at least two or more epoxy groups as the cationic polymerization reactive group and contains 20% by mass or more and 100% by mass or less of a compound having a reactive group equivalent of 150 g/eq or more and 300 g/eq or less.

5. The curable resin composition according to claim 1, wherein the cationic polymerizable compound (B) has two or more and six or less cationic polymerization reactive groups.

6. The curable resin composition according to claim 1, wherein the rubber particle (C) is contained at 2 parts by mass or more and 70 parts by mass or less, based on 100 parts by mass of total mass of the oxetane compound (A) and the cationic polymerizable compound (B).

7. The curable resin composition according to claim 1, wherein the curing agent (D) is a photocationic polymerization initiator.

8. The curable resin composition according to claim 7, wherein the photocationic polymerization initiator is contained at 0.1 parts by mass or more and 15 parts by mass or less, based on 100 parts by mass of total mass of the oxetane compound (A) and the cationic polymerizable compound (B).

9. The curable resin composition according to claim 1, further comprising 0 parts by mass or more and 80 parts by mass or less of a radical polymerizable compound, based on 100 parts by mass of total mass of the oxetane compound (A) and the cationic polymerizable compound (B).

10. The curable resin composition according to claim 9, wherein the radical polymerizable compound is a (meth)acrylate compound.

11. The curable resin composition according to claim 9, wherein a radical polymerization initiator is contained at 0.1 parts by mass or more and 15 parts by mass or less, based on 100 parts by mass of the radical polymerizable compound.

12. A manufacturing method of a three-dimensional object by photocuring the curable resin composition according to claim 1, based on a slice data of a three-dimensional model, the method comprising:

forming a layer formed of the curable resin composition; and

irradiating the layer formed of the curable resin composition with an active energy ray based on the slice data to cure the curable resin composition.

13. The manufacturing method of a three-dimensional object according to claim 12, wherein the active energy ray is an ultraviolet ray of a wavelength of 300 nm or more and 450 nm or less.

14. The manufacturing method of a three-dimensional object according to claim 12, wherein the active energy ray is concentrated in a dot shape and is used to scan, and the layer formed of the curable resin composition is irradiated with the active energy ray to cure the layer formed of the curable resin composition.

15. The manufacturing method of a three-dimensional object according to claim 12, wherein the active energy ray is irradiated in a planar shape through a planar plotting mask to cure the layer formed of the curable resin composition.