Curable composition and cured product

Patent metadata

Field	Value
Publication number	US-10927199-B2
Application number	US-201815993002-A
Country	US
Kind code	B2
Filing date	May 30, 2018
Priority date	Dec 9, 2015
Publication date	Feb 23, 2021
Grant date	Feb 23, 2021

Abstract

To provide a curable composition whereby it is possible to obtain a cured product having a high Abbe number and being excellent in transparency, crack resistance and releasability; and such a cured product. A curable composition comprises, in specific ratios, surface-modified metal oxide particles (A) having (meth)acryloyl-group-containing surface-modifying groups on the surface of the metal oxide particles, a compound (B) having a fluorine atom and at least one (meth)acryloyl group, a compound (C) having a urethane bond or —OCH2CH(OH)CH2—, having at least two (meth)acryloyl groups and having a mass-average molecular weight of at least 1,000, a compound (D) having no unsaturated bond-containing ring structure and having at least one (meth)acryloyl group, and a polymerization initiator (E).

First claim

What is claimed is:

1. A curable composition, comprising
surface-modified metal oxide particles (A), which are metal oxide particles having (meth)acryloyl group-containing surface-modifying groups on surface thereof,
a compound (B) which is a (meth)acryloyl group-containing compound comprising a fluorine atom,
a compound (C) which is a (meth)acryloyl group-containing compound comprising at least two (meth)acryloyl-containing groups and said (meth)acryloyl-containing group comprises a urethane bond or —OCH 2 CH(OH)CH 2 —, and having a mass average molecular weight of at least 1,000,
a compound (D) which is a (meth)acryloyl group-containing compound comprising at least one (meth)acryloyl-containing group and said (meth)acryloyl-containing group comprises no unsaturated bond-containing ring structure, and
a polymerization initiator (E),
wherein
per 100 mass % of a total mass of said particles (A), said component (B), said component (C), and said component (D), said particles (A) are from 20 to 45 mass %, said compound (B) is from 0.01 to 20 mass %, said compound (C) is from 10 to 50 mass %, and said compound (D) is from 10 to 50 mass %, and
said polymerization initiator (E) is from 0.01 to 10 parts by mass per 100 parts by mass of the total mass of said particles (A), said component (B), said component (C), and said component (D).

2. The curable composition according to claim 1 , wherein the (meth)acryloyl group-containing surface modifying groups have a group represented by formula (A1),
CH 2 ═CR 1 C(O)—X—(CH 2 ) a —SiR 2 b (—*) 3-b   (A1)

where * is a bond of Si, R 1 is a hydrogen atom or a methyl group, R 2 is a hydrogen atom or a C 1-4 hydrocarbon group, X is —O— or —NH—, a is an integer of from 2 to 7, and b is an integer of from 0 to 2, provided that when b is 2, the two R 2 are the same or different.

3. The curable composition according to claim 1 , wherein the metal oxide particles of the surface-modified metal oxide particles (A) are silica particles.

4. The curable composition according to claim 1 , wherein a median diameter of the surface-modified metal oxide particles (A) is from 1 to 1,000 nm.

5. The curable composition according to claim 1 , wherein the compound (B) is a fluoro(meth)acrylate.

6. The curable composition according to claim 1 , wherein the compound (C) is
a compound (C1) having a urethane bond and having at least two (meth)acryloyl groups, or
a compound (C2) having —OCH 2 CH(OH)CH 2 — and having at least two (meth)acryloyl groups.

7. The curable composition according to claim 6 , wherein the compound (C) is the compound (C1), which is a compound represented by formula (C11):
{(CH 2 ═CR 11 C(O)O—) i J-OC(O)NH—} k Q  (C11)

where R 11 is a hydrogen atom or a methyl group, i is 1 or 2, J is a (i+1)-valent organic group, and Q is a k-valent organic group.

8. The curable composition according to claim 6 , wherein the compound (C) is the compound (C2), which is a compound represented by formula (C21):
CH 2 ═CR 21 C(O)O—CH 2 CH(OH)CH 2 —(O) s —} t G  (C21)

where R 21 is a hydrogen atom or a methyl group, s is 0 or 1, t is an integer of at least 2, and G is a t-valent organic group.

9. The curable composition according to claim 1 , wherein the compound (D) is
a compound (D1) having no unsaturated bond-containing ring structure and having one (meth)acryloyloxy group, or
a compound (D2) having no unsaturated bond-containing ring structure and having at least two (meth)acryloyloxy groups.

10. The curable composition according to claim 9 , wherein the compound (D) is the compound (D1), which is an acrylic acid ester or a methacrylic acid ester.

11. The curable composition according to claim 9 , wherein the compound (D) is the compound (D2), which is a (meth)acrylate of a diol, a (meth)acrylate of a triol, or a tetraol (meth)acrylate.

12. The curable composition according to claim 1 , wherein the polymerization initiator (E) is a photo-radical polymerization initiator.

13. The curable composition according to claim 1 , further comprising
a solvent containing at least one member selected from the group consisting of an ester, a ketone, a hydroxyl group, and an ether.

14. The curable composition according to claim 1 , which has a viscosity at 25° C. of from 100 to 15,000 mPa·s.

15. A cured product, obtained by a process comprising
curing the curable composition according to claim 1 .

16. The curable composition according to claim 1 , wherein a proportion of said particles (A) ranges from 27.1 to 43.1 mass % per 100 mass % of the total mass of said particles (A), said component (B), said component (C), and said component (D).

17. The curable composition according to claim 1 , wherein a proportion of said compound (B) ranges from 1.7 to 9.4 mass % per 100 mass % of the total mass of said particles (A), said component (B), said component (C), and said component (D).

18. The curable composition according to claim 1 , wherein a proportion of said compound (C) ranges from 11.6 to 45.3 mass % per 100 mass % of the total mass of said particles (A), said component (B), said component (C), and said component (D).

19. The curable composition according to claim 1 , wherein a proportion of said compound (D) ranges from 24.7 to 49.6 mass % per 100 mass % of the total mass of said particles (A), said component (B), said component (C), and said component (D).

20. The curable composition according to claim 1 , wherein said compound (D) has an alicylic structure.

21. The curable composition according to claim 1 , wherein compound (C) does not contain a compound having a urethane bond.

Assignees

• Agc Inc

Inventors

• Takagi Keisuke
• Yoshida Jun
• Murofushi Hidenobu

Classifications

• C08F20/14 Primary

  Methyl esters {, e.g. methyl (meth)acrylate} · CPC title

• C08F292/00 Primary

  Macromolecular compounds obtained by polymerising monomers on to inorganic materials · CPC title

• C08F2/48

  by ultraviolet or visible light · CPC title

• C08F30/08

  containing silicon · CPC title

• C09C1/36

  Compounds of titanium {(C09C1/0009, C09C1/0015, C09C1/0078 take precedence)} · CPC title