Polyorganosilsesquioxane, hard coat film, adhesive sheet, and laminate

Patent metadata

Field	Value
Publication number	US-2016297933-A1
Application number	US-201415100733-A
Country	US
Kind code	A1
Filing date	Nov 14, 2014
Priority date	Dec 13, 2013
Publication date	Oct 13, 2016
Grant date	—

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

1 - 20 . (canceled)

21 . A 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,
the polyorganosilsesquioxane comprising
a constitutional unit represented by Formula (1),

the polyorganosilsesquioxane having 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 a total amount (100% by mole) of all siloxane constitutional units,
the polyorganosilsesquioxane having 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,

Formulae (1), (I), (II), and (4) expressed as follows:
[Chem. 1]
[R 1 SiO 3/2 ]  (1)

wherein R 1 represents an epoxy-containing group,
[Chem. 2]
[R a SiO 3/2 ]  (I)

wherein R a is selected from an epoxy-containing 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, and a hydrogen atom,
[Chem. 3]
[R b SiO(OR c )]  (II)

wherein R b is selected from an epoxy-containing 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, and a hydrogen atom; and R c is selected from a hydrogen atom and a C 1 -C 4 alkyl group, and
[Chem. 4]
[R 1 SiO(OR c )]  (4)

wherein R 1 is as defined in Formula (1); and R c is as defined in Formula (II).

22 . The polyorganosilsesquioxane according to claim 21 , further comprising
a constitutional unit represented by Formula (2):
[Chem. 5]
[R 2 SiO 3/2 ]  (2)

wherein R 2 is selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted alkenyl group.

23 . The polyorganosilsesquioxane according to claim 21 ,
wherein R 1 is selected from:
a group represented by Formula (1a);
a group represented by Formula (1b);
a group represented by Formula (1c); and
a group represented by Formula (1d),
Formulae (1a), (1b), (1c), and (1d) expressed as follows:

wherein R 1a represents a straight or branched chain alkylene group,

wherein R 1b represents a straight or branched chain alkylene group,

wherein R 1c represents a straight or branched chain alkylene group,

wherein R 1d represents a straight or branched chain alkylene group.

24 . The polyorganosilsesquioxane according to claim 22 ,
wherein R 2 is a substituted or unsubstituted aryl group.

25 . A curable composition comprising:
the polyorganosilsesquioxane according to claim 21 .

26 . The curable composition according to claim 25 , further comprising
a curing catalyst.

27 . The curable composition according to claim 26 ,
wherein the curing catalyst comprises a cationic photoinitiator.

28 . The curable composition according to claim 26 ,
wherein the curing catalyst comprises a cationic thermal initiator.

29 . The curable composition according to claim 25 , further comprising
a vinyl ether compound.

30 . The curable composition according to claim 25 , further comprising
a vinyl ether compound containing a hydroxy group in molecule.

31 . The curable composition according to claim 25 , as a curable composition for formation of a hard coat layer.

32 . The curable composition according to claim 25 , as an adhesive composition.

33 . A cured product of the curable composition according to claim 25 .

34 . A hard coat film comprising:
a substrate; and a hard coat layer disposed on or over at least one side of the substrate, the hard coat layer being a layer of a cured product of the curable composition according to claim 31 .

35 . The hard coat film according to claim 34 ,
wherein the hard coat layer has a thickness of 1 to 200 μm.

36 . The hard coat film according to claim 34 ,
wherein the hard coat film is producible by a roll-to-roll process.

37 . The hard coat film according to claim 34 , further comprising
a surface-protecting film on or over the hard coat layer.

38 . A method for producing a hard coat film, the method comprising the steps of:
(A) unwinding a wound, rolled substrate; (B) applying the curable composition according to claim 31 to at least one side of the unwound substrate, and curing the applied curable composition to form a hard coat layer on the substrate to thereby give a hard coat film; and (C) rewinding the hard coat film into a roll, the steps (A), (B), and (C) being performed successively.

39 . An adhesive sheet comprising:
a substrate; and an adhesive layer disposed on or over the substrate, the adhesive layer being a layer of the curable composition according to claim 32 .

40 . 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 curable composition according to claim 32 .

Assignees

• Daicel Corp

Inventors

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

Classifications

• C08J7/0427

  with only one layer of a composition containing a polymer binder (with more layers C08J7/042) · CPC title

• C09D183/06

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

• C08G59/68

  characterised by the catalysts used · CPC title

• B32B2250/05

  5 or more layers · CPC title

• C09J2483/00

  Presence of polysiloxane · CPC title