Anti-fogging film-forming material, coating liquid for forming anti-fogging film, anti-fogging article, and methods for producing these

Patent metadata

Field	Value
Publication number	US-9765224-B2
Application number	US-201314385065-A
Country	US
Kind code	B2
Filing date	Feb 20, 2013
Priority date	Mar 13, 2012
Publication date	Sep 19, 2017
Grant date	Sep 19, 2017

Abstract

Disclosed is an antifogging film-forming material obtained by reacting, in the presence of a quaternary ammonium salt or quaternary phosphonium salt, a copolymer represented by a certain general formula with a multifunctional epoxy compound having a solubility of 40-100 mass % in 25° C. water. The antifogging film-forming material is characterized by having a weight average molecular weight of 100,000-5,000,000. With this material, it becomes possible to obtain an antifogging article excellent in antifogging property, heat resistance, chemical resistance and abrasion resistance.

First claim

The invention claimed is:

1. An antifogging film-forming material obtained by reacting, in the presence of a quaternary ammonium salt or quaternary phosphonium salt, a compound represented by the following general formula [1] with a multifunctional epoxy compound having a solubility of 40-100 mass % in 25° C. water, the antifogging film-forming material being characterized by having a weight average molecular weight of 100,000-5,000,000;

wherein R 1 and R 2 represent a hydrogen or a methyl group, and R 3 represents a hydrogen or a C 1 -C 5 alkyl group;

wherein X represents
at least one group selected from the group consisting of —C(═O)—N(R 4 ) 2 where R 4 is mutually independently a C 1 -C 4 alkyl group, an amino group, a sulfonate group and hydroxyl group; or
a monovalent organic group comprising at least one group selected from the group consisting of an amide group, an amino group, a sulfonate group and hydroxyl group and an aliphatic hydrocarbon group;
wherein Y represents a carboxyl group or a group represented by —R 5 —C(═O)—OH where R 5 is a divalent aliphatic hydrocarbon group or a divalent organic group comprising at least one group selected from the group consisting of an ester group, an ether group and an amide group and an aliphatic hydrocarbon group; and
wherein “a” and “b” are integers at the ratio of a:b=0.7-2.5:1.0 and wherein the order of repeating structural units is not particularly limited.

2. The antifogging film-forming material as claimed in claim 1 , wherein the compound represented by the general formula [1] is a compound represented by the following general formula [2];

wherein “X”, wherein “a” and “b” are the same as in the formula [1], wherein “m” represents an integer of 0-2, wherein “n” represents an integer of 0-3, wherein “s” represents an integer of 1-4, and wherein “t” represents an integer of 1-4 and wherein the order of repeating structural units is not particularly limited.

3. The antifogging film-forming material as claimed in claim 1 , wherein the compound represented by the general formula [1] has a weight average molecular weight of 10,000-500,000.

4. The antifogging film-forming material as claimed in claim 1 , wherein the multifunctional epoxy compound is an aliphatic glycidyl ether-based polyepoxide or an aliphatic glycidyl ether-based epoxide.

5. The antifogging film-forming material as claimed in claim 1 , wherein the multifunctional epoxy compound has an average number of functional groups per molecule of 1.5-6.5.

6. The antifogging film-forming material as claimed in claim 1 , wherein the Y in the compound represented by the general formula [1] is a carboxyl group, by reacting the multifunctional epoxy compound in an amount of epoxy group of 1-2 mol relative to 1 mol of the carboxyl group.

7. A coating liquid, comprising the antifogging film-forming material as claimed in claim 1 and a solvent.

8. The coating liquid, as claimed in claim 7 , further comprising a curing agent.

9. The coating liquid, as claimed in claim 7 , further comprising fine particles.

10. A method for preparing the coating liquid-as claimed in claim 7 , comprising
(a) reacting the compound represented by the general formula [1] with the multifunctional epoxy compound in the solvent and in the presence of the quaternary ammonium salt or quaternary phosphonium salt; and
at least one operation selected from the group consisting of
(b) adjusting solid matter concentration and viscosity by concentrating a solution containing the antifogging film-forming material obtained in the step (a), or adding a solvent to the solution containing the antifogging film-forming material obtained in the step (a),
(c) adding the curing agent to the solution containing the antifogging film-forming material obtained in the step (a), and
(d) adding fine particles to the solution containing the-antifogging film-forming material obtained in the step (a).

11. An antifogging article comprising a base material, a primer layer formed on the surface thereof, and an antifogging film formed on the surface of the primer layer, wherein the antifogging film is obtained by applying the coating liquid as claimed in claim 7 on the surface of the primer layer and curing the coating liquid.

12. The antifogging article as claimed in claim 11 , wherein haze values of the antifogging article, measured before and after carrying out an abrasion resistance test according to JIS R 3212 at a portion where the test is conducted, have a difference of not larger than 4.0.

13. The antifogging article as claimed in claim 11 , wherein an antifogging property reduction, which is a value expressed by (A−B)×100/A where B is water absorption under water absorption saturation condition per unit area of the antifogging film after being exposed to 100° C. heat for 1000 hours and A is water absorption under water absorption saturation condition per unit area of the antifogging film before the exposure is 40% or less.

14. The antifogging article as claimed in claim 13 , wherein the water absorption A is 0.2-5 mg/cm 2 .

15. A method for producing the antifogging article as claimed in claim 11 , comprising:
(a) forming the primer layer on the surface of the base material, wherein the primer layer comprises a silane coupling agent;
(b) applying the coating liquid onto the primer layer; and
(c) curing a coating film obtained by the step (b).

16. The method for producing the antifogging article, as claimed in claim 15 , wherein the step (c) is conducted by heating the coating film obtained after the step (b) at not higher than 80° C., thereby curing the coating film.

17. The method for producing the antifogging article, as claimed in claim 15 , further comprising:
(d) rinsing the surface of the antifogging film after the step (c).

18. The method for producing the antifogging article, as claimed in claim 15 , further comprising:
(e) forming an overcoat layer having a density of 0.50-0.85 g/cm 2 on the surface of the antifogging film after the step (c) and before the step (d).

19. The antifogging article as claimed in claim 11 , further comprising an overcoat layer having a density of 0.50-0.85 g/cm 2 , on the surface of the antifogging film.

20. An antifogging article as claimed in claim 19 , wherein the overcoat layer comprises a reactant of polyacrylic acids having a weight average molecular weight of 2,000-150,000 and a multifunctional epoxy compound having a solubility of 40-100 mass % in 25° C. water.

Assignees

• Central Glass Co Ltd

Inventors

• Takimoto Chiharu
• Hirano Toshihiro
• Ashida Toru
• Oonishi Nozomi

Classifications

• C08F220/54

  Amides {, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide} · CPC title

• C03C17/326

  Epoxy resins · CPC title

• C09D163/00

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title

• Y10T428/31515

  As intermediate layer · CPC title

• C03C17/34

  with at least two coatings having different compositions (C03C17/44 takes precedence) · CPC title