Polyorganosilsesquioxane, hard coat film, adhesive sheet, and laminate

Patent metadata

Field	Value
Publication number	US-11560453-B2
Application number	US-202117394031-A
Country	US
Kind code	B2
Filing date	Aug 4, 2021
Priority date	Dec 13, 2013
Publication date	Jan 24, 2023
Grant date	Jan 24, 2023

Abstract

Provided is a polyorganosilsesquioxane capable of forming, when cured, a cured product that offers high surface hardness and good heat resistance, is highly flexible, and has excellent processability. The present invention relates to a polyorganosilsesquioxane including a constitutional unit represented by Formula (1). The polyorganosilsesquioxane includes a constitutional unit represented by Formula (I) and a constitutional unit represented by Formula (II) in a mole ratio of the constitutional unit represented by Formula (I) to the constitutional unit represented by Formula (II) of 5 or more. The polyorganosilsesquioxane has a total proportion of the constitutional unit represented by Formula (1) and a constitutional unit represented by Formula (4) of 55% to 100% by mole based on the total amount (100% by mole) of all siloxane constitutional units. The polyorganosilsesquioxane has a number-average molecular weight of 1000 to 3000 and a molecular-weight dispersity (weight-average molecular weight to number-average molecular weight ratio) of 1.0 to 3.0.

[R 1 SiO 3/2 ]  (1)

[Chem. 2]

[R a SiO 3/2 ]  (I)

[Chem. 3]

[R b SiO(OR c )]  (II)

[Chem. 4]

[R 1 SiO(OR c )]  (4)

First claim

The invention claimed is:

1. An adhesive layer comprising a curable composition comprising a polyorganosilsesquioxane,
the polyorganosilsesquioxane comprising:
a constitutional unit represented by Formula (I); and
a constitutional unit represented by Formula (II),
in a mole ratio of the constitutional unit represented by Formula (I) to the constitutional unit represented by Formula (II) of from 5 to 18,
a constitutional unit represented by Formula (2),

the polyorganosilsesquioxane having a total proportion of the constitutional unit represented by Formula (I) and the constitutional unit represented by formula (II) of 95% to 99% by mole based on a total amount (100% by mole) of all siloxane constitutional units,
the polyorganosilsesquioxane having a number-average molecular weight of 1100 to 2600 and a molecular-weight dispersity (weight-average: molecular weight to number-average molecular weight ratio) of 1.1 to 2.0, Formulae (I), (II), and (2) expressed as follows:
[R a SiO 3/2 ]  (I)

wherein R a is selected from:
a group represented by Formula (1a);
a group represented by Formula (1d),

Formulae (1a) and (1d) expressed as follows:

wherein R 1a represents an ethylene group,

wherein R 1d represents an ethylene group,
[R b SiO(OR c )]  (II)

wherein R b is selected from:
a group represented by Formula (1a); and
a group represented by Formula (1d),

Formulae (1a) and (1d) expressed as follows:

wherein R 1a represents an ethylene group,

wherein R 1d represents an ethylene group, and R c is selected from a hydrogen atom and a C 1 -C 4 alkyl group, and
[R 2 SiO 3/2 ]  (2)

wherein R 2 is an unsubstituted phenyl group.

2. The adhesive layer according to claim 1 ,
the curable composition further comprising
a curing catalyst.

3. The adhesive layer according to claim 2 ,
wherein the curing catalyst comprises a cationic photoinitiator.

4. The adhesive layer according to claim 2 ,
wherein the curing catalyst comprises a cationic thermal initiator.

5. The adhesive layer according to claim 1 ,
the curable composition further comprising
a vinyl ether compound.

6. The adhesive layer according to claim 1 ,
the curable composition further comprising
a vinyl ether compound containing a hydroxy group in molecule.

7. An adhesive sheet comprising:
a substrate; and
the adhesive layer according to claim 1 disposed on or over the substrate.

8. The adhesive sheet according to claim 7 ,
wherein the substrate is a semiconductor substrate.

9. A laminate comprising
three or more layers,
the three or more layers comprising:
two adherend layers; and
an adhesive layer disposed between the two adherend layers, the adhesive layer being a layer of a cured product of the adhesive layer according to claim 1 .

10. The laminate according to claim 9 ,
wherein the adherend layer is a semiconductor substrate.

11. A method for producing a laminate comprising three or more layers, the three or more layers comprising two adherend layers and an adhesive layer disposed between the two adherend layers, the method comprising the steps of:
forming the adhesive layer according to claim 1 on an adherend layer;
applying another adherend layer to the formed adhesive layer to obtain a resulting article; and
subjecting the resulting article to light irradiation and/or heating to cure the adhesive layer.

Assignees

• Daicel Corp

Inventors

• Kuwana Akihiro
• Harada Nobuhiko
• Masui Maya
• Takase Ichiro
• Maetani Shinji
• Tsuji Naoko

Classifications

• C08G77/14 Primary

  containing silicon bound to oxygen-containing groups · CPC title

• B32B2250/02

  2 layers · CPC title

• B32B2255/26

  Polymeric coating · CPC title

• B32B15/08

  of synthetic resin · CPC title

• C08G59/24

  carbocyclic · CPC title