Weather-resistant hard coat composition for glass-substitute substrate, cured product, and laminate

Patent metadata

Field	Value
Publication number	US-2022017776-A1
Application number	US-201917295527-A
Country	US
Kind code	A1
Filing date	Nov 20, 2019
Priority date	Nov 21, 2018
Publication date	Jan 20, 2022
Grant date	—

Abstract

The purpose of the present invention is to provide a weather-resistant hard coat composition for a glass-substitute substrate capable of efficiently forming a coating film excelling in weather resistance, scratch resistance, and toughness. The present invention provides: a weather-resistant hard coat composition for a glass-substitute substrate, the composition containing a polyorganosilsesquioxane having a constituent unit represented by Formula (1); a cured product thereof; and a laminate having a glass-substitute substrate and a coating film formed on at least one surface of the glass-substitute substrate. The coating film is a layer of a cured product of the weather-resistant hard coat composition for a glass-substitute substrate. [In formula (1), R1 represents a group containing an active energy ray-curable functional group.]

First claim

1 . A weather-resistant hard coat composition for a glass-substitute substrate, the composition comprising a polyorganosilsesquioxane having a constituent unit represented by Formula (1):
[R 1 SiO 3/2 ]  (1)
where, R 1 represents a group containing an active energy ray-curable functional group.

2 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , wherein the polyorganosilsesquioxane further comprises:
a constituent unit represented by Formula (I):
[R a SiO 3/2 ]  (I)

where, R a represents a group containing an active energy ray-curable functional group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a hydrogen atom; and a constituent unit represented by Formula (II):
[R b SiO 2/2 (OR c )]  (II)

where, R b represents a group containing an active energy ray-curable functional group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a hydrogen atom, and R c represents a hydrogen atom or an alkyl group having from 1 to 4 carbons; and a molar ratio [(constituent unit represented by Formula (I))/(constituent unit represented by Formula (II))] of the constituent unit represented by Formula (I) to the constituent unit represented by Formula (II) is from 5 to 500.

3 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , wherein a number average molecular weight of the polyorganosilsesquioxane is from 1000 to 50000.

4 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , wherein the polyorganosilsesquioxane further comprises a constituent unit represented by Formula (4):
[R 1 SiO 2/2 (OR c )]  (4)
where, R 1 is the same as in Formula (1), and R c is the same as in Formula (II), and a ratio of the constituent unit represented by Formula (1) and the constituent unit represented by the Formula (4) with respect to a total amount (100 mol %) of siloxane constituent units is from 55 to 100 mol %.

5 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , wherein a molecular weight dispersity, weight average molecular weight/number average molecular weight, of the polyorganosilsesquioxane is from 1.0 to 4.0.

6 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , wherein the polyorganosilsesquioxane further comprises a constituent unit represented by Formula (2):
[R 2 SiO 3/2 ]  (2)
where, R 2 represents a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted alkenyl group.

7 . The weather-resistant hard coat composition for a glass-substitute substrate according claim 6 , wherein the R 2 represents a substituted or unsubstituted aryl group.

8 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , wherein the active energy ray-curable functional group is an epoxy group.

9 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , wherein the R 1 is:
a group represented by Formula (1a):

where, R 1a represents a linear or branched alkylene group;
a group represented by Formula (1b):

where, R 1b represents a linear or branched alkylene group;
a group represented by Formula (1c):

where, R 1c represents a linear or branched alkylene group; or
a group represented by Formula (1d):

where, R 1d represents a linear or branched alkylene group.

10 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , wherein the active energy ray-curable functional group is a (meth)acryloxy group.

11 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , further comprising a photocuring catalyst.

12 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 11 , wherein the photocuring catalyst is a photocationic polymerization initiator.

13 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 11 , wherein the photocuring catalyst is a photoradical polymerization initiator.

14 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , further comprising a compound having one or more (meth)acryloxy groups per molecule.

15 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , further comprising at least one type selected from the group consisting of ultraviolet absorbers and antioxidants.

16 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , further comprising a compound having one or more thermally-polymerizable functional groups and one or more photopolymerizable functional groups per molecule.

17 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , further comprising a fluorine-containing photopolymerizable resin.

18 . The weather-resistant hard coat composition for a glass-substitute substrate according to claim 1 , wherein the glass-substitute substrate is an automotive headlight cover or an automotive window glass.

19 . A cured product of the weather-resistant hard coat composition for a glass-substitute substrate described in claim 1 .

20 . A laminate comprising a glass-substitute substrate and a coating film formed on at least one surface of the glass-substitute substrate, wherein the coating film is a layer of the cured product described in claim 19 .

21 . The laminate according to claim 20 , wherein a thickness of the coating film is from 0.1 to 1000 μm.

22 . The laminate according to claim 20 , wherein the laminate is used for an automotive headlight cover or for an automotive window glass.

23 . A weather-resistant hard coat composition for a glass-substitute substrate, wherein a below-defined pencil hardness of a cured product obtained by curing the composition under the following curing conditions is not less than H, a color difference (ΔE) as defined below is less than 20, and a glossiness retention rate as defined below is not less than 15%,
Curing conditions
Pre-baking: at 150° C. for 2 minutes
UV radiation: radiation dosage: 400 mJ/cm 2 , radiation intensity: 260 mW/cm 2
Aging: at 120° C. for 0.5 hours
Pencil hardness
Measured in accordance with JIS K5600-5-4 (750 g load).
Color difference (ΔE)
The color difference (ΔE) is

Assignees

• Daicel Corp

Inventors

• Shimizu Kunio
• Takahashi Hiroshi
• Shibamoto Akihiro

Classifications

• Y10T428/31

  Surface property or characteristic of web, sheet or block · CPC title

• Y10T428/26

  Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension · CPC title

• Y10T428/31663

  As siloxane, silicone or silane · CPC title

• C08F299/08

  from polysiloxanes · CPC title

• C08F290/068

  Polysiloxanes · CPC title