Curable resin composition, cured product, diffractive optical element, multilayer diffractive optical element, and method for producing curable resin composition

Patent metadata

Field	Value
Publication number	US-11377545-B2
Application number	US-202017020305-A
Country	US
Kind code	B2
Filing date	Sep 14, 2020
Priority date	Mar 15, 2018
Publication date	Jul 5, 2022
Grant date	Jul 5, 2022

Abstract

The present invention provides a curable resin composition including a bifunctional or more (meth)acrylate compound, indium tin oxide particles, and an acidic polymer, in which the acidic polymer has a moiety including a carboxyl group at a polymer skeleton of a (meth)acrylate compound and at any one of terminals of the polymer skeleton of a (meth)acrylate compound, and an acid value of the acidic polymer is 2.0 mgKOH/g or more and less than 100 mgKOH/g. The curable resin composition of the present invention provides a transparent cured product, hardly causes bubbles to be mixed in a case of applying the curable resin composition to a mold so as to form a lattice-shaped cured product, and also has a good peeled surface shape from the mold after curing. The present invention also provides a diffractive optical element including a surface having a diffraction grating shape and formed of the cured product of the curable resin composition.

First claim

What is claimed is:

1. A curable resin composition comprising:
a bifunctional or more (meth)acrylate compound;
indium tin oxide particles; and
an acidic polymer,
wherein the acidic polymer has a moiety including a carboxyl group at a polymer skeleton of a (meth)acrylate compound and at any one of terminals of the polymer skeleton of a (meth)acrylate compound,
the acid value of the acidic polymer is 2.0 mgKOH/g or more and less than 100 mgKOH/g, and
the acidic polymer is represented by Formula (1),
(R 1 —S—L 2 ) n —L 1 —(L 3 —A—R 2 ) m . . . (1)

wherein in Formula (1), R 1 represents a substituent including at least one carboxyl group, A represents a polymer skeleton of a (meth)acrylate compound, R 2 represents a hydrogen atom or a substituent not including a carboxyl group, L 1 represents a single bond or a (m+n)-valent linking group, L 2 and L 3 each independently represents a single bond or a divalent linking group, m represents an integer of 1 to 8, and n represents an integer of 1 to 9, in which m+n satisfies 2 to 6, each of n, R 1 , and L 2 may be the same as or different from each other, and each of m, R 2 , A, and L 3 may be the same as or different from each other.

2. The curable resin composition according to claim 1 ,
wherein the moiety of the acidic polymer includes the following partial structure,

3. The curable resin composition according to claim 1 ,
wherein the weight-average molecular weight of the acidic polymer is 1,000 to 20,000.

4. The curable resin composition according to claim 1 ,
wherein the content of the acidic polymer is 5% by mass to 50% by mass with respect to the total mass of the indium tin oxide particles.

5. The curable resin composition according to claim 1 ,
wherein the content of the indium tin oxide particles is 10% by mass to 60% by mass with respect to the total mass of the curable resin composition.

6. The curable resin composition according to claim 1 ,
wherein the particle size of the indium tin oxide particles is 5 nm to 50 nm.

7. The curable resin composition according to claim 1 , further comprising:
a photopolymerization initiator.

8. A method for producing the curable resin composition according to claim 1 , the method comprising:
a step of preparing a dispersion liquid in which the indium tin oxide particles are dispersed in a solvent having a constituent (δp) 0 to 6 MPa( 1/2 ), the constituent being a polarity term in an SP value;
a step of obtaining a mixed solution by mixing the dispersion liquid with the bifunctional or more (meth)acrylate compound and the acidic polymer; and
a step of distilling off the solvent from the mixed solution.

9. The producing method according to claim 8 ,
wherein the solvent is selected from the group consisting of toluene, xylene, and hexane.

10. The producing method according to claim 8 ,
wherein the solvent is toluene.

11. The producing method according to claim 8 ,
wherein the indium tin oxide particles in the dispersion liquid are surface-modified with a monocarboxylic acid having 6 to 20 carbon atoms.

12. The producing method according to claim 11 ,
wherein the monocarboxylic acid is oleic acid.

13. The producing method according to claim 8 , further comprising:
a step of further mixing a photopolymerization initiator to a mixture obtained after the distillation.

14. A cured product of the curable resin composition according to claim 1 ,
wherein the refractive index at a wavelength of 587.56 nm is 1.40 to 1.57, and the Abbe number is 15 to 25.

15. A diffractive optical element comprising:
the cured product according to claim 14 ,
wherein the diffractive optical element includes a surface having a diffraction grating shape and formed of the cured product.

16. A multilayer diffractive optical element comprising:
a first diffractive optical element; and
a second diffractive optical element,
wherein the first diffractive optical element is the diffractive optical element according to claim 15 , and
the surface of the first diffractive optical element, which has a diffraction grating shape, and a surface of the second diffractive optical element, which has a diffraction grating shape, face each other.

17. The multilayer diffractive optical element according to claim 16 ,
wherein the refractive index of the second diffractive optical element at a wavelength of 587.56 nm is 1.55 to 1.70, and is larger than the refractive index of the first diffractive optical element at the wavelength of 587.56 nm, and
the Abbe number of the second diffractive optical element is 35 to 60.

18. The multilayer diffractive optical element according to claim 16 ,
wherein the surface of the first diffractive optical element, which has a diffraction grating shape, and the surface of the second diffractive optical element, which has a diffraction grating shape, are in contact with each other.

19. The multilayer diffractive optical element according to claim 16 , further comprising:
a transparent substrate,
wherein the first diffractive optical element, the second diffractive optical element, and the transparent substrate are arranged in this order.

Assignees

• Fujifilm Corp

Inventors

• Nagai Takayasu
• Shiraiwa Naozumi
• Nakayama Takafumi
• Morooka Naoyuki
• Takata Masahiro
• Fujiwara Masanori

Classifications

• C08L33/02 Primary

  Homopolymers or copolymers of acids; Metal or ammonium salts thereof · CPC title

• C08K9/04

  Ingredients treated with organic substances {(treated with macromolecular compounds C08K9/08)} · CPC title

• C08L33/22

  Homopolymers or copolymers of nitriles containing four or more carbon atoms · CPC title

• C08F20/12

  of monohydric alcohols or phenols · CPC title

• C08F20/38

  Esters containing sulfur · CPC title