# US 10,308,850 B2 · Curable composition, method for manufacturing curable composition, cured product, method for using curable composition, and optical device

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- Number: US 10,308,850 B2
- Document ID: US10308850B2
- Status: Granted
- Kind: B2
- Application number: 15/328,239
- Filed: 2015-07-23
- Published: 2017-07-27
- Granted: 2019-06-04
- Earliest claimed: 2014-07-23
- Assignees: Lintec Corporation
- Applicants: Lintec Corporation
- Inventors: Mikihiro Kashio; Masami Matsui; Yae Ishikawa; Hidekazu Nakayama
- Web page: https://patentgrep.com/patent/US10308850B2

## CPC

- C09J 183/04: Polysiloxanes
- C08K 5/5435: containing oxygen in a ring
- C08K 5/544: containing nitrogen
- C08K 5/5455: containing at least one [IMAGE cpc-sch-C08K-1012.gif] group
- C08K 5/5477: {containing nitrogen in a heterocyclic ring}
- C08K 5/548: containing sulfur {(C08K5/5477 takes precedence)}
- C08L 83/06: containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence)
- C09J 11/06: organic
- C09J 183/00: Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09K 3/10: {Materials in mouldable or extrudable form} for sealing or packing joints or covers (filling pastes C09D5/34)
- H10F 77/50: Encapsulations or containers (for photovoltaic modules H10F19/80)
- H10H 20/854: characterised by their material, e.g. epoxy or silicone resins
- C08G 77/04: Polysiloxanes
- C08G 77/18: to alkoxy or aryloxy groups
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10F: INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
- H10H: INORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The present invention is a curable composition comprising a component (A) and a component (B), the curable composition producing a cured product that has a solid-state Si nuclear magnetic resonance spectrum in which a peak is observed within a range from −80 ppm or more to less than −40 ppm, and a half-width of the peak is 500 to 900 Hz, the component (A) being a curable polysilsesquioxane compound that comprises a repeating unit represented by a formula (a-1), R1SiO3/2 (a-1) the component (B) being at least one silane coupling agent selected from a group consisting of a silane coupling agent that comprises a nitrogen atom in its molecule, and a silane coupling agent that comprises an acid anhydride structure in its molecule, and a method for producing the curable composition, and a cured product, and a method for using the curable composition, and an optical device.

## Claims

### Claim 1

A curable composition comprising a component (A) and a component (B),
the curable composition producing a cured product that has a solid-state Si nuclear magnetic resonance spectrum in which a peak is observed within a range from −80 ppm or more to less than −40 ppm, and a half-width of the peak is 500 to 900 Hz,
the component (A) being a curable polysilsesquioxane compound that comprises a repeating unit represented by a formula (a-1),
R1SiO3/2 (a-1)
wherein R1 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group, and
the component (B) being at least one silane coupling agent selected from a group consisting of a silane coupling agent that comprises a nitrogen atom in its molecule, and a silane coupling agent that comprises an acid anhydride structure in its molecule.

### Claim 2 (depends on 1)

The curable composition according to claim 1, wherein R1 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

### Claim 3 (depends on 1)

The curable composition according to claim 1, wherein the curable polysilsesquioxane compound that is used as the component (A) has a mass average molecular weight (Mw) of 1,000 to 30,000.

### Claim 4 (depends on 1)

The curable composition according to claim 1, wherein the curable polysilsesquioxane compound that is used as the component (A) is a curable polysilsesquioxane compound obtained by subjecting at least one compound represented by a formula (a-2) to polycondensation in the presence of a polycondensation catalyst,
R1Si(OR2)x(X1)3-x (a-2)
wherein R1 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group, R2 is an alkyl group having 1 to 10 carbon atoms, X1 is a halogen atom, and x is an integer from 0 to 3, provided that a plurality of R2 are either identical to or different from each other when a plurality of R2 are present, and a plurality of X1 are either identical to or different from each other when a plurality of X1 are present.

### Claim 5 (depends on 1)

The curable composition according to claim 1, wherein the component (B) comprises both the silane coupling agent that comprises a nitrogen atom in its molecule, and the silane coupling agent that comprises an acid anhydride structure in its molecule.

### Claim 6 (depends on 1)

The curable composition according to claim 1, the curable composition comprising the component (A) and the component (B) in a mass ratio (component (A):component (B)) of 100:0.01 to 100:50.

### Claim 7 (depends on 1)

A method for producing the curable composition according to claim 1, comprising:
a step (I) that subjects at least one compound represented by a formula (a-2) to polycondensation in the presence of a polycondensation catalyst to obtain the curable polysilsesquioxane compound,
R1Si(OR2)x(X1)3-x (a-2)
wherein R1 is the same as defined above, R2 is an alkyl group having 1 to 10 carbon atoms, X1 is a halogen atom, and x is an integer from 0 to 3, provided that a plurality of R2 are either identical to or different from each other when a plurality of R2 are present, and a plurality of X1 are either identical to or different from each other when a plurality of X1 are present; and
a step (II) that mixes the curable polysilsesquioxane compound obtained by the step (I) with at least one silane coupling agent selected from the group consisting of the silane coupling agent that comprises a nitrogen atom in its molecule, and the silane coupling agent that comprises an acid anhydride structure in its molecule.

### Claim 8 (depends on 7)

The method according to claim 7, wherein at least an acid catalyst is used as the polycondensation catalyst.

### Claim 9 (depends on 8)

The method according to claim 8, wherein the acid catalyst is at least one compound selected from phosphoric acid, hydrochloric acid, boric acid, citric acid, acetic acid, sulfuric acid, and methanesulfonic acid.

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 10)

The cured product according to claim 10, the cured product being an optical element-securing material.

### Claim 12 (depends on 1)

An optical element securing adhesive, comprising the curable composition according to claim 1 as an optical element-securing adhesive.

### Claim 13 (depends on 1)

An optical element sealing material, comprising the curable composition according to claim 1 as an optical element sealing material.

### Claim 14 (depends on 1)

An optical device produced using the curable composition according to claim 1 as an optical element-securing adhesive or an optical element sealing material.