Curable composition, method for producing curable composition, cured product, use of curable composition, and optical device

Patent metadata

Field	Value
Publication number	US-10920117-B2
Application number	US-201615780537-A
Country	US
Kind code	B2
Filing date	Dec 21, 2016
Priority date	Dec 22, 2015
Publication date	Feb 16, 2021
Grant date	Feb 16, 2021

Abstract

The invention is a curable composition comprising the following component (A) and component (B):
Component (A): a curable polysilsesquioxane compound having a repeating unit represented by the following specific formula (a-1):

R 1 —D—SiO 3/2   (a-1)
Component (B): a silane coupling agent having a nitrogen atom in its molecule, and a method for producing the curable composition, and a cured product obtained by curing the curable composition, and a method for using the curable composition as an adhesive for an optical element-fixing material, and a method for using the curable composition as a sealant for an optical element-fixing material, and an optical device obtained by using the curable composition as an adhesive or a sealant for an optical element-fixing material. One aspect of the curable composition according to one embodiment of the invention can provide a cured product excellent in adhesiveness and heat resistance and having a low refractive index.

First claim

The invention claimed is:

1. A thermally curable composition comprising the following component (A) and component (B):
Component (A): a curable polysilsesquioxane compound having a repeating unit represented by the following formula (a-1):
R 1 -D-SiO 3/2   (a-1)

wherein R 1 represents a fluoroalkyl group represented by a compositional formula: C x H (2x−y+1) F y , x represents an integer of 1 to 10, and y represents an integer of 2 to (2x+1), D represents a linking group (excluding an alkylene group) for connecting R 1 and Si, or a single bond,
having a mass-average molecular weight (Mw) of 800 to 20,000,
Component (B): a silane coupling agent having a nitrogen atom in its molecule, and
the component (B) being a compound represented by the following formula (b-3) or (b-4),

wherein R a represents an alkoxy group having 1 to 6 carbon atoms, and each of t1 to t5 independently represents an integer of 1 to 10.

2. The thermally curable composition according to claim 1 , wherein the curable polysilsesquioxane compound of the component (A) further has a repeating unit represented by the following formula (a-2),
R 2 SiO 3/2   (a-2)

wherein R 2 represents an unsubstituted alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms with or without substituents.

3. The thermally curable composition according to claim 2 , wherein R 2 is an unsubstituted alkyl group having 1 to 10 carbon atoms in the repeating unit represented by formula (a-2).

4. The thermally curable composition according to claim 2 , wherein the component (A) comprises the repeating unit represented by formula (a-1) and the repeating unit represented by formula (a-2) in a molar ratio [repeating unit represented by formula (a-1)]: [repeating unit represented by formula (a-2)] of 5:95 to 100:0.

5. The thermally curable composition according to claim 1 , wherein the component (A) is obtained by polycondensing a compound represented by the following formula (a-3), or compounds represented by the following formulas (a-3) and (a-4) in the presence of a polycondensation catalyst,
R 1 -D-Si(OR 3 ) p (X 1 ) 3−p   (a-3)

R 2 Si(OR 4 ) q (X 2 ) 3−q   (a-4)

wherein R 1 , R 2 and D represent the same as described above, each of R 3 and R 4 independently represents an alkyl group having 1 to 10 carbon atoms, each of X 1 and X 2 independently represents a halogen atom, each of p and q independently represents an integer of 0 to 3, each of the plural R 3 , R 4 , X 1 and X 2 may be the same or different from each other.

6. The thermally curable composition according to claim 1 , which further comprises a diluent.

7. The thermally curable composition according to claim 6 , wherein the total amount of the component (A) and the component (B) is 50 to 100 mass % based on the whole components excluding the diluent in the thermally curable composition.

8. The thermally curable composition according to claim 1 , wherein the solid content of the curable composition is 50 mass % to less than 100 mass %.

9. A method for producing the curable composition according to claim 1 , having the following steps (I) and (II):
Step (I): the step of obtaining the curable polysilsesquioxane compound by polycondensing a compound represented by the following formula (a-3), or compounds represented by the following formulas (a-3) and (a-4) in the presence of the polycondensation catalyst:
R 1 -D-Si(OR 3 ) p (X 1 ) 3−p   (a-3)

R 2 Si(OR 4 ) q (X 2 ) 3−q   (a-4)

wherein R 1 , R 2 and D represent the same groups as described above, each of R 3 and R 4 independently represents an alkyl group having 1 to 10 carbon atoms, each of X 1 and X 2 independently represents a halogen atom, each of p and q independently represents an integer of 0 to 3, each of the plural R 3 , R 4 , X 1 and X 2 may be the same or different from each other,
Step (II): the step of mixing the curable polysilsesquioxane compound obtained in the step (I) with the component (B).

10. A cured product obtained by thermal curing the thermally curable composition according to claim 1 .

11. The cured product according to claim 10 which is an optical element-fixing material.

12. A method for using the thermally curable composition according to claim 1 as an adhesive, said method comprising applying the thermosetting composition to a surface of an optical element or a surface of a substrate, press-bonding the optical element and substrate together, and thermal curing to adhere said optical element with said substrate.

13. A method for using the thermally curable composition according to claim 1 as a sealant, said method comprising molding the thermosetting composition with an optical element to make a formed article, and thermal curing the formed article to make an optical element sealant.

14. An optical device obtained by using the thermally curable composition according to claim 1 as an adhesive or a sealant for an optical element-fixing material.

Assignees

• Lintec Corp

Inventors

• Nanashima Yutaka
• Nakayama Hidekazu
• Miyawaki Manabu
• Kashio Mikihiro

Classifications

• C09J183/08 Primary

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• H10W74/476

  Organic materials comprising silicon · CPC title

• C08G77/24 Primary

  halogen-containing groups · CPC title

• C08G2170/00

  Compositions for adhesives · CPC title

• C08G77/385

  containing halogens · CPC title