IP Library Granted Patent US 11,400,693
Granted Patent B2
US 11,400,693 · App. 16/469,342 · Granted Aug 2, 2022

Weather resistance improver, resin composition for coating metal-nanowire layer, and metal nanowire-containing laminate

Inventor: Toshiyuki Hasegawa (Ichihara, JP)
Assignee: SEIKO PMC CORPORATION
B32B27/281B32B15/02B32B17/10B32B27/08B32B27/18B32B27/36C08F2/44C08K5/47C08K5/5313C08K5/5317C08K5/5377C08L67/00C09D5/00C09D167/00H01B1/22B32B2260/023B32B2264/104B32B2305/72B32B2307/202
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Quick Facts
Patent No.
US 11,400,693
App. No.
16/469,342
Granted
Aug 2, 2022
Kind
B2
Abstract

The present disclosure relates to a weather resistance improver including a compound (A) and a compound (B), wherein the compound (A) is a compound having the following structure (1), and the compound (B) is a compound having the following structure (2) or a salt thereof. According to the weather resistance improver, it is possible to suppress deterioration of a transparent conductive film using metal nanowires even under any conditions of long-term exposure to sunlight, long-term exposure to artificial light, and high-temperature/high-humidity.

Claims (57)

1. A weather resistance improver comprising a compound (A) and a compound (B), wherein

the compound (A) is a compound having the following structure (1), and

the compound (B) is a compound having the following structure (2) or a salt thereof,

2. The weather resistance improver according to claim 1 , comprising:

the compound (A); and

the compound (B) in which at least one hydroxy group is bonded to one phosphorus atom, wherein

the compound (A) is a compound represented by the following general formula (1) and/or (2), and

the compound (B) is at least one selected from phytic acid, compounds represented by the following general formulas (3), (4), (5) and (6), and salts thereof,

(where, in the general formula (1), R 1 represents a hydrogen atom, an alkyl group of 1 to 8 carbon atoms or a (di)carboxyalkyl group having an alkyl group of 1 to 3 carbon atoms)

(where, in the general formula (2), R 2 represents a hydrogen atom, an alkyl group of 1 to 8 carbon atoms or a (di)carboxyalkyl group having an alkyl group of 1 to 3 carbon atoms)

(where, in the general formula (3), R 3 and R 4 each represents a hydrogen atom, or an alkyl group, an arylalkyl group, a hydroxyalkyl group, an alkoxyalkyl group, a carboxyalkyl group, an aminoalkyl group, in which an alkyl moiety has 1 to 8 carbon atoms, or an alkenyl group, an aryl group, a hydroxyaryl group or an alkoxyaryl group, and R 3 and R 4 may be the same or different)

(where, in the general formula (4), R 5 is a hydrogen atom, or an alkyl group, an arylalkyl group, a hydroxyalkyl group, an alkoxyalkyl group, a carboxyalkyl group, an aminoalkyl group, in which an alkyl moiety has 1 to 8 carbon atoms, or a vinyl group, an aryl group, an arylalkenyl group, a hydroxyaryl group, an alkoxyaryl group or a carboxyalkyl group, and R 6 represents a hydrogen atom, or an alkyl group, an arylalkyl group, a hydroxyalkyl group, an alkoxyalkyl group, a carboxyalkyl group, an aminoalkyl group, a perfluoroalkyl group, in which an alkyl moiety has 1 to 8 carbon atoms, or an aryl group, a hydroxyaryl group, an alkoxyaryl group or a carboxyaryl group)

(where, in the general formula (5), R 7 and R 8 each represents a hydrogen atom, or an alkyl group, an arylalkyl group, a hydroxyalkyl group, an alkoxyalkyl group, a carboxyalkyl group, an aminoalkyl group, in which an alkyl moiety has 1 to 8 carbon atoms, or an aryl group, a hydroxyaryl group, alkoxyaryl group, carboxyaryl group or (meth)acryloyloxyalkyl group, and R 7 and R 8 may be the same or different)

(where, in the general formula (6), R 9 represents a hydrogen atom or a hydroxy group, R 10 represents a hydrogen atom, an alkyl group or an aminoalkyl group of 1 to 5 carbon atoms, and n represents 1 to 12).

3. The weather resistance improver according to claim 1 , wherein the compound (A) is at least one selected from a group consisting of 2-mercaptothiazoline, 3-(2-benzothiazol-2-ylthio)propionic acid, and (1,3-benzothiazol-2-ylthio) succinic acid.

4. The weather resistance improver according to claim 1 , wherein the compound (B) is at least one selected from a group consisting of phosphinic acid, dialkylphosphinic acid having 1 to 8 carbon atoms, (2-carboxyethyl) phenylphosphinic acid, phenylphosphinic acid, diphenylphosphinic acid, bis(4-methoxyphenyl) phosphinic acid, methylphenylphosphinic acid and phenylvinylphosphinic acid.

5. A resin composition for coating a silver nanowire-containing layer, comprising the weather resistance improver according to claim 1 , a photopolymerization initiator and/or a thermal polymerization initiator, and polymerizable monomers and/or macromonomers.

6. The resin composition for coating the silver nanowire-containing layer according to claim 5 , comprising at least one compound (A) of 0.3 to 4 mass %, and at least one compound (B) of 0.03 to 0.6 mmol/g as an amount of phosphorus atom with respect to the polymerizable monomers and/or macromonomers.

7. A silver nanowire-containing laminate comprising: a silver nanowire-containing layer; and a protective layer disposed on the silver nanowire-containing layer and for protecting the silver nanowire-containing layer, wherein

the weather resistance improver according to claim 1 is contained only in the protective layer, or in both the protective layer and the silver nanowire-containing layer, and

the protective layer is a cured product of a resin composition for coating the silver nanowire-containing layer, which further satisfies the following conditions:

(1) containing a photopolymerization initiator and/or a thermal polymerization initiator, and polymerizable monomers and/or macromonomers;

(2) containing at least one compound (A) of 0.3 to 4 mass % with respect to the polymerizable monomers and/or macromonomers; and

(3) containing at least one compound (B) of 0.03 to 0.6 mmol/g as an amount of phosphorus atom with respect to the polymerizable monomers and/or macromonomers.

8. The silver nanowire-containing laminate according to claim 7 , wherein the silver nanowire-containing layer comprises a polyester resin dissolved or dispersed in an aqueous solvent or an aqueous dispersion medium.

9. The weather resistance improver according to claim 1 , wherein

the compound (A) is at least one selected from a group consisting of 2-mercaptothiazoline, 2-mercaptobenzothiazole, 3-(1,3-benzothiazol-2-ylthio) propionic acid and (1,3-benzothiazol-2-ylthio) succinic acid, and

the compound (B) is at least one selected from a group consisting of phytic acid, phosphoric acid, dibutyl phosphate, 2-(acryloyloxy)ethyl phosphate, bis[2-(methacryloyloxy) ethyl]phosphate, acid phosphoxy polyethylene glycol mono(meth)acrylate, acid phosphoxy polyepropylene glycol mono(meth)acrylate, phosphonic acid, octylphosphonic acid, phenylphosphonic acid, vinylphosphonic acid, 6-phosphonohexanoic acid, (12-phosphonododecyl) phosphonic acid, etidronic acid, phosphinic acid, dimethylphosphinic acid, diisooctylphosphinic acid, phenylphosphinic acid, diphenylphosphinic acid, (2-carboxyethyl) phenylphosphinic acid, bis(4-methoxyphenyl) phosphinic acid, bis(hydroxymethyl) phosphinic acid, methylphenylphosphinic acid and phenylvinylphosphinic acid.

10. The weather resistance improver according to claim 9 , wherein

the compound (A) is 2-mercaptothiazoline.

11. The weather resistance improver according to claim 9 , wherein the compound (B) is at least one selected from a group consisting of phosphinic acid, dimethylphosphinic acid, diisooctylphosphinic acid, phenylphosphinic acid, diphenylphosphinic acid, (2-carboxyethyl) phenylphosphinic acid, bis(4-methoxyphenyl) phosphinic acid, bis(hydroxymethyl) phosphinic acid, methylphenylphosphinic acid and phenylvinylphosphinic acid.

12. A silver nanowire-containing laminate comprising: a silver nanowire-containing layer; and a protective layer disposed on the silver nanowire-containing layer and for protecting the silver nanowire-containing layer, wherein

the weather resistance improver according to claim 11 is contained only in the protective layer, or in both the protective layer and the silver nanowire-containing layer, and

the protective layer is a cured product of a resin composition for coating the silver nanowire-containing layer, which further satisfies the following conditions:

(1) containing a photopolymerization initiator and/or a thermal polymerization initiator, and polymerizable monomers and/or macromonomers;

(2) containing at least one compound (A) of 0.3 to 4 mass % with respect to the polymerizable monomers and/or macromonomers; and

(3) containing at least one compound (B) of 0.03 to 0.6 mmol/g as an amount of phosphorus atom with respect to the polymerizable monomers and/or macromonomers.

13. A silver nanowire-containing laminate comprising: a silver nanowire-containing layer; and a protective layer disposed on the silver nanowire-containing layer and for protecting the silver nanowire-containing layer, wherein

the weather resistance improver according to claim 10 is contained only in the protective layer, or in both the protective layer and the silver nanowire-containing layer, and

the protective layer is a cured product of a resin composition for coating the silver nanowire-containing layer, which further satisfies the following conditions:

(1) containing a photopolymerization initiator and/or a thermal polymerization initiator, and polymerizable monomers and/or macromonomers;

(2) containing at least one compound (A) of 0.3 to 4 mass % with respect to the polymerizable monomers and/or macromonomers; and

(3) containing at least one compound (B) of 0.03 to 0.6 mmol/g as an amount of phosphorus atom with respect to the polymerizable monomers and/or macromonomers.

14. A silver nanowire-containing laminate comprising: a silver nanowire-containing layer; and a protective layer disposed on the silver nanowire-containing layer and for protecting the silver nanowire-containing layer, wherein

the weather resistance improver according to claim 11 is contained only in the protective layer, or in both the protective layer and the silver nanowire-containing layer, and

the protective layer is a cured product of a resin composition for coating the silver nanowire-containing layer, which further satisfies the following conditions:

(1) containing a photopolymerization initiator and/or a thermal polymerization initiator, and polymerizable monomers and/or macromonomers;

(2) containing at least one compound (A) of 0.3 to 4 mass % with respect to the polymerizable monomers and/or macromonomers; and

(3) containing at least one compound (B) of 0.03 to 0.6 mmol/g as an amount of phosphorus atom with respect to the polymerizable monomers and/or macromonomers.

15. The silver nanowire-containing laminate according to claim 12 , wherein

the resin composition for coating the silver nanowire-containing layer contains at least one compound (A) of 0.5 to 3 mass % with respect to the polymerizable monomers and/or macromonomers, and contains at least one compound (B) of 0.06 to 0.5 mmol/g as an amount of phosphorus atom with respect to the polymerizable monomers and/or macromonomers.

16. The silver nanowire-containing laminate according to claim 12 , wherein

the resin composition for coating the silver nanowire-containing layer contains at least one compound (A) of 0.5 to 3 mass % with respect to the polymerizable monomers and/or macromonomers, and contains at least one compound (B) of 0.07 to 0.4 mmol/g as an amount of phosphorus atom with respect to the polymerizable monomers and/or macromonomers.

17. The silver nanowire-containing laminate according to claim 1 , wherein a neutralization ratio of the compound (B) is 80% or less based on atomic groups represented by P—OH.

18. The silver nanowire-containing laminate according to claim 1 , wherein a neutralization ratio of the compound (B) is 50% or less based on atomic groups represented by P—OH.

19. The silver nanowire-containing laminate according to claim 1 , wherein a neutralization ratio of the compound (B) is 20% or less based on atomic groups represented by P—OH.

20. The silver nanowire-containing laminate according to claim 14 , wherein the silver nanowire-containing layer contains the compound (A).

Assignments (2)
CHANGE OF NAME Recorded Nov 6, 2025
From: SEIKO PMC CORPORATION
To: CHEMIPAZ CORPORATION
Reel/Frame 073511/0092 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 13, 2019
From: HASEGAWA, TOSHIYUKI
To: SEIKO PMC CORPORATION
Reel/Frame 049459/0697 →
Priority Claims (1)
JP JP2016-246587 · Dec 20, 2016 · national
Continuity (1)
Related Publication 20190299575A1 · Oct 3, 2019