Hardcoat film, article and image display device having hardcoat film, and method for manufacturing hardcoat film

Patent metadata

Field	Value
Publication number	US-11530334-B2
Application number	US-202017010125-A
Country	US
Kind code	B2
Filing date	Sep 2, 2020
Priority date	Mar 30, 2018
Publication date	Dec 20, 2022
Grant date	Dec 20, 2022

Abstract

A hardcoat film includes a substrate; a hardcoat layer; and an anti-scratch layer, where the hardcoat layer includes a cured product of polyorganosilsesquioxane, the polyorganosilsesquioxane has a siloxane constitutional unit containing a (meth)acryloyl group and a siloxane constitutional unit containing an epoxy group and is represented by the General Formula (1), a film thickness of the anti-scratch layer is 0.05 to 5 μm, and the anti-scratch layer includes a cured product of a compound having two or more (meth)acryloyl groups in one molecule, where Ra represents a group containing a (meth)acryloyl group; Rb represents a group containing an epoxy group; Rc represents a monovalent substituent; p, q, and r represent a proportion of Ra, Rb, and Rc in the General Formula (1) respectively; p+q+r is 100; p and q are greater than 0; r is equal to or greater than 0; p/q is 0.01 to 99.

First claim

What is claimed is:

1. A hardcoat film comprising:
a substrate;
a hardcoat layer; and
an anti-scratch layer,
wherein the hardcoat layer includes a cured product of polyorganosilsesquioxane, the polyorganosilsesquioxane is represented by the following General Formula (1), a film thickness of the anti-scratch layer is 1 μm to 5 μm, and the anti-scratch layer includes a cured product of a compound having two or more (meth)acryloyl groups in one molecule,

wherein, in the General Formula (1), [SiO 1.5 ] represents a silsesquioxane portion in the polyorganosilsesquioxane; Ra represents a group containing a (meth)acryloyl group; Rb represents a group containing an epoxy group; Rc represents a monovalent substituent or a plurality of Rc's may form a bond with each other; p, q, and r represent a proportion of Ra, Rb, and Rc in the General Formula (1) respectively; p+q+r is 100; p and q are greater than 0; r is equal to or greater than 0; p/q is 0.01 to 99; in a case where there are a plurality of Ra's, a plurality of Rb's, and a plurality of Rc's in the General Formula (1), the plurality of Ra's may be the same as or different from each other, the plurality of Rb's may be the same as or different from each other, and the plurality of Rc's may be the same as or different from each other; and in a case where there is a plurality of Rc's in the General Formula (1), the plurality of Rc's may form a bond with each other,
wherein a content rate of the cured product of the compound having two or more (meth)acryloyl groups in one molecule with respect to the total mass of the antiscratch layer is equal to or higher than 80% by mass, and
wherein the compound having two or more (meth)acryloyl groups in one molecule is polyorganosilsesquioxane having (meth)acryloyl groups and is represented by the following General Formula (2),

wherein, in the General Formula (2), Ra represents a group containing a (meth)acryloyl group; Rc represents a monovalent substituent; Ra, Rc, and [SiO 1.5 ] are defined as in Formula (1); t and u represent a proportion of each of Ra and Rc in the General Formula (2); t+u=100; t is greater than 0; u is equal to or greater than 0; in a case where there are a plurality of Ra's and a plurality of Rc's in the General Formula (2), the plurality of Ra's may be the same as or different from each other and the plurality of Rc's may be the same as or different from each other; and in a case where there is a plurality of Rc's in the General Formula (2), the plurality of Rc's may form a bond with each other.

2. The hardcoat film according to claim 1 ,
wherein Rb in the General Formula (1) is a group having a condensed ring structure of an epoxy group and an alicyclic group.

3. The hardcoat film according to claim 2 ,
wherein the group having a condensed ring structure of an epoxy group and an alicyclic group is a group having an epoxycyclohexyl group.

4. The hardcoat film according to claim 1 ,
wherein in the General Formula (1), (p+q)/(p+q+r) is 0.5 to 1.0.

5. The hardcoat film according to claim 2 ,
wherein in the General Formula (1), (p+q)/(p+q+r) is 0.5 to 1.0.

6. The hardcoat film according to claim 3 ,
wherein in the General Formula (1), (p+q)/(p+q+r) is 0.5 to 1.0.

7. The hardcoat film according to claim 1 ,
wherein in the General Formula (1), p/q is 0.5 to 2.0.

8. The hardcoat film according to claim 2 ,
wherein in the General Formula (1), p/q is 0.5 to 2.0.

9. The hardcoat film according to claim 1 ,
wherein in the General Formula (1), there is a plurality of Rc's, the plurality of Rc's form a bond with each other, and r/(p+q+r) is 0.005 to 0.20.

10. The hardcoat film according to claim 2 ,
wherein in the General Formula (1), there is a plurality of Rc's, the plurality of Rc's form a bond with each other, and r/(p+q+r) is 0.005 to 0.20.

11. The hardcoat film according to claim 1 ,
wherein a weight-average molecular weight of the polyorganosilsesquioxane represented by General Formula (1) is 2,000 to 20,000.

12. The hardcoat film according to claim 2 ,
wherein a weight-average molecular weight of the polyorganosilsesquioxane represented by General Formula (1) is 2,000 to 20,000.

13. The hardcoat film according to claim 1 ,
wherein a film thickness of the hardcoat layer is 1 to 50 μm.

14. The hardcoat film according to claim 2 ,
wherein a film thickness of the hardcoat layer is 1 to 50 I lm.

15. The hardcoat film according to claim 1 ,
wherein the substrate is a plastic substrate.

16. An article comprising: the hardcoat film according to claim 1 .

17. An image display device comprising: the hardcoat film according to claim 1 as a surface protection film.

18. A method for manufacturing a hardcoat film, comprising:
(I) coating a substrate with a composition for forming a hardcoat layer including polyorganosilsesquioxane so as to form a coating film (i) on the substrate;
(II) performing a curing treatment on the coating film so as to form a hardcoat layer;
(III) coating the hardcoat layer with a composition for forming an anti-scratch layer including a compound having two or more (meth)acryloyl groups in one molecule so as to form a coating film (ii) on the hardcoat layer, said anti-scratch layer having a film thickness of 1 μm to 5 μm; and
(IV) performing a curing treatment on the coating film (ii) so as to form an anti-scratch layer,
wherein the polyorganosilsesquioxane is represented by the following General Formula (1),

wherein, in the General Formula (1), [SiO 1.5 ] represents a silsesquioxane portion in the polyorganosilsesquioxane; Ra represents a group containing a (meth)acryloyl group; Rb represents a group containing an epoxy group; Rc represents a monovalent substituent or a plurality of Rc's may form a bond with each other; p, q, and r represent a proportion of Ra, Rb, and Rc in the General Formula (1) respectively; p+q+r is 100; p and q are greater than 0; r is equal to or greater than 0; p/q is 0.01 to 99; in a case where there are a plurality of Ra's, a plurality of Rb's, and a plurality of Rc's in the General Formula (1), the plurality of Ra's may be the same as or different from each other, the plurality of Rb's may be the same as or different from each other, and the plurality of Rc's may be the same as or different from each other; and in a case where there is a plurality of Rc's in the General Formula (1), the plurality of Rc's may form a bond with each other, wherein a content rate of the cured product of the compound having two or more (meth)acryloyl groups in one molecule with respect to the total mass of the antiscratch layer is equal to or higher than 80% by mass, and wherein the compound having two or more (meth)acryloyl groups in one molecule is polyorganosilsesquioxane having (meth)acryloyl groups and is represented by the following General Formula (2),

wherein, in the General Formula (2), Ra represents a group containing a (meth)acryloyl group; Rc represents a monovalent substituent; Ra, Rc, and [SiO 1.5 ] are defined as in Formula (1); t and u represent a proportion of each of Ra and Rc in the General Formula (2); t+u=100; t is greater tha

Assignees

• Fujifilm Corp

Inventors

• Kitamura Tetsu
• Tamura Akio
• Fukushima Yuta

Classifications

• C08K5/0025

  Crosslinking or vulcanising agents; including accelerators · CPC title

• C08G77/14

  containing silicon bound to oxygen-containing groups · CPC title

• B32B27/08

  of synthetic resin · CPC title

• C08J7/046

  Forming abrasion-resistant coatings; Forming surface-hardening coatings · CPC title

• C09D183/06 Primary

  containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence) · CPC title