Thermosetting resin composition for coating metal thin film and metal laminate using the same

Patent metadata

Field	Value
Publication number	US-11459449-B2
Application number	US-201816606108-A
Country	US
Kind code	B2
Filing date	Dec 12, 2018
Priority date	Dec 14, 2017
Publication date	Oct 4, 2022
Grant date	Oct 4, 2022

Abstract

The present invention relates to a thermosetting resin composition for coating a metal film having excellent crack resistance and a metal laminate using the same.

First claim

The invention claimed is:

1. A thermosetting resin composition for coating a metal film comprising:
an amine compound containing at least one functional group selected from the group consisting of a sulfone group, a carbonyl group, a halogen group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, and an alkylene group having 1 to 20 carbon atoms;
wherein the amine compound may include at least one compound selected from the group consisting of the following Chemical Formulas 1 to 3:

wherein, in Chemical Formula 1,
A is a sulfone group, a carbonyl group, or an alkylene group having 1 to 10 carbon atoms,
X 1 to X 8 are ach independently a nitro group, a cyano group, a hydrogen atom, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms,
R 1 , R 1 ′ , R 2 and R 2 ′ are each independently a hydrogen atom, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms,
and n is an integer of 1 to 10,
in which the alkylene group having 1 to 10 carbon atoms, the alkyl group having 1 to 6 carbon atoms, the aryl group having 6 to 15 carbon atoms, or the heteroaryl group having 2 to 20 carbon atoms are each independently substituted with a nitro group, a cyano group, or a halogen group,

wherein, in Chemical Formula 2,
Y 1 to Y 8 are each independently a nitro group, a cyano group, a hydrogen atom, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms,
R 3 , R 3 ′, R 4 , and R 4 ′ are each independently a hydrogen atom, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms, and
m is an integer of 1 to 10,
in which the alkyl group having 1 to 6 carbon atoms, the aryl group having 6 to 15 carbon atoms, and the heteroaryl group having 2 to 20 carbon atoms are each independently substituted with at least one functional group selected from the group consisting of a nitro group, a cyano group, and a halogen group,

wherein, in Chemical Formula 3,
Z 1 to Z 4 are each independently a nitro group, a cyano group, a hydrogen atom, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms, and
R 5 , R 5 ′, R 6 , and R 6 ′ are each independently a hydrogen atom, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms,
in which the alkyl group having 1 to 6 carbon atoms, the aryl group having 6 to 15 carbon atoms, and the heteroaryl group having 2 to 20 carbon atoms are each independently substituted with at least one functional group selected from the group consisting of a nitro group, a cyano group, and a halogen group;

a binder resin containing an epoxy resin and a bismaleimide resin;
an inorganic filler; and
a rubber-based component,
wherein the rubber-based component includes at least one rubber selected from the group consisting of a styrene-butadiene-based rubber, a neoprene-based rubber, a nitrile-based rubber, a butyl-based rubber, a butadiene-based rubber, an ethylene propylene-based rubber, a silicone-based rubber, a urethane-based rubber, and an acrylic-based rubber,
the rubber-based component is contained in an amount of 5 parts by weight or more and less than 40 parts by weight, based on 100 parts by weight in total of the amine compound and the binder resin, and
when the viscosity of the thermosetting resin composition is measured in a temperature range of 90 to 180° C. using a rheometer, the lowest viscosity in the temperature range satisfies the condition of a complex viscosity of 3500 Pa·s or less.

2. The thermosetting resin composition for coating a metal film according to claim 1 , wherein the rubber-based component is at least one rubber selected from the group consisting of a butadiene-based rubber, a silicone-based rubber, and an acrylic-based rubber.

3. The thermosetting resin composition for coating a metal film according to claim 1 , wherein the rubber-based component is contained at 5 to 15 parts by weight based on 100 parts by weight in total of the amine compounds and binder resin.

4. The thermosetting resin composition for coating a metal film according to claim 1 , wherein the acrylic-based rubber has a weight average molecular weight of 30×10 4 to 65×10 4 , and comprises: (i) an acrylic acid ester copolymer containing a repeating unit derived from butyl acrylate and a repeating unit derived from acrylonitrile; (ii) an acrylic acid ester copolymer containing repeating units derived from butadiene; or (iii) a repeating unit derived from an alkyl acrylate containing a linear or branched alkyl group having 2 to 10 carbon atoms.

5. The thermosetting resin composition for coating a metal film according to claim 1 , wherein the silicone-based rubber comprises: (i) a copolymer including an epoxy group or a polyether-modified silicone repeating unit, or (ii) a silicone repeating unit in which a terminal group is substituted with an amine group or an epoxy group, and wherein the silicone-based rubber has a weight average molecular weight of 1×10 3 to 5×10 4 .

6. The thermosetting resin composition for coating a metal thin film according to claim 1 , wherein the butadiene-based rubber comprises: (i) a copolymer including a butadiene repeating unit in which a terminal group is substituted with a hydroxy group, (ii) a butadiene repeating unit containing an acrylic group, or (iii) a butadiene repeating unit containing an epoxy group, and wherein the butadiene-based rubber has a weight average molecular weight of 1×10 3 to 5×10 4 .

7. The thermosetting resin composition for coating a metal film according to claim 1 ,
wherein the content of the inorganic filler is 200 parts by weight or more, based on 100 parts by weight in total of the amine compound and the binder resin.

8. The thermosetting resin composition for coating a metal film according to claim 1 ,
wherein the content of the amine compound is 15 to 60% by weight, based on the total weight of the amine compound and the binder resin.

9. The thermosetting resin composition for coating a metal film according to claim 1 ,
wherein the content of the epoxy resin is 30 to 80% by weight and the content of the bismaleimide resin is 1 to 20% by weight, based on the total weight of the amine compound and the binder resin.

10. The thermosetting resin composition for coating a metal film according to claim 1 ,
wherein the inorganic filler is at least one compound selected from the group consisting of silica, aluminum trihydroxide, magnesium hydroxide, molybdenum oxide, zinc molybdate, zinc borate, zinc stannate, alumina, clay, kaolin, talc, calcined kaolin, calcined talc, mica, short glass fiber, glass fine powder, and hollow glass.

Assignees

• Lg Chemical Ltd

Inventors

• Yun Minhyuk
• Min Hyunsung
• Kim Young Chan
• Shim Hee Yong
• Shim Changbo
• Son Gilsang

Classifications

• C09D7/47

  Levelling agents · CPC title

• C08L19/00

  Compositions of rubbers not provided for in groups C08L7/00 - C08L17/00 · CPC title

• C09D163/00 Primary

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

• C08L23/22

  Copolymers of isobutene; Butyl rubber; Homopolymers or copolymers of other iso-olefins · CPC title

• C08L9/02

  Copolymers with acrylonitrile · CPC title