# US 4,396,679 A · Plastic articles suitable for electroless plating

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- Number: US 4,396,679 A
- Document ID: US4396679A
- Status: Granted
- Kind: A
- Application number: 06/274,502
- Filed: 1981-06-16
- Granted: 1983-08-02
- Earliest claimed: 1980-06-18
- Assignees: Mitsubishi Gas Chemical Company, Inc.
- Inventors: Morio Gaku; Yukiya Masuda; Akira Katata; Kanzi Ishikawa; Nobuyuki Ikeguchi
- Web page: https://patentgrep.com/patent/US4396679A

## CPC

- H05K 3/387: {for electroless plating (H05K3/4661 takes precedence)}
- C08J 7/0427: {with only one layer of a composition containing a polymer binder (with more layers C08J7/042)}
- C08J 7/043: Improving the adhesiveness of the coatings per se, e.g. forming primers (adhesives in the form of films or foils characterised by the primer layers between the polymer carriers and the adhesives C09J7/50)
- C08K 5/315: Compounds containing carbon-to-nitrogen triple bonds
- C23C 18/20: of organic surfaces, e.g. resins
- C23C 18/206: {Use of metal other than noble metals and tin, e.g. activation, sensitisation with metals (sensitising with tin C23C18/285, sensitising with noble metals C23C18/30)}
- C23C 18/208: {with use of metal first}
- C23C 18/24: using acid aqueous solutions
- C23C 18/28: Sensitising or activating
- C08J 2421/00: Characterised by the use of unspecified rubbers
- H05K 3/181: {by electroless plating (adhesives therefor H05K3/387)}
- H05K 2201/0133: Elastomeric or compliant polymer
- Y10T 428/31507: Of polycarbonate
- Y10T 428/31511: Of epoxy ether
- Y10T 428/31554: Next to second layer of polyamidoester
- Y10T 428/31562: Next to polyamide [nylon, etc.]
- Y10T 428/31565: Next to polyester [polyethylene terephthalate, etc.]
- Y10T 428/31569: Next to natural rubber
- Y10T 428/31573: Next to addition polymer of ethylenically unsaturated monomer
- Y10T 428/31587: Hydrocarbon polymer [polyethylene, polybutadiene, etc.]
- Y10T 428/31598: Next to silicon-containing [silicone, cement, etc.] layer
- Y10T 428/31605: Next to free metal
- Y10T 428/31667: Next to addition polymer from unsaturated monomers, or aldehyde or ketone condensation product
- Y10T 428/31721: Of polyimide
- Y10T 428/31728: Next to second layer of polyamide
- Y10T 428/31732: At least one layer is nylon type
- Y10T 428/31797: Next to addition polymer from unsaturated monomers
- Y10T 428/31833: Next to aldehyde or ketone condensation product or addition polymer from unsaturated monomers
- Y10T 428/31855: Of addition polymer from unsaturated monomers
- Y10T 428/31862: Melamine-aldehyde
- Y10T 428/3187: Amide-aldehyde
- Y10T 428/31913: Monoolefin polymer
- Y10T 428/31917: Next to polyene polymer
- Y10T 428/31928: Ester, halide or nitrile of addition polymer
- H05K: PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C23C: COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL (making metal-coated products by extrusion B21C23/22; covering with metal by connecting pre-existing layers to articles, see the relevant places, e.g. B21D39/00, B23K; metallising of glass C03C; metallising mortars, concrete, artificial stone, ceramics or natural stone C04B41/00; enamelling of, or applying a vitreous layer to, metals C23D; treating metal surfaces or coating of metals by electrolysis or electrophoresis C25D; single-crystal film growth C30B; by metallising textiles D06M11/83; decorating textiles by locally metallising D06Q1/04)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

A plastic article in which a semi-cured or cured product of a curable resin composition comprising a mixture and/or a preliminary reaction product of (a) at least one cyanate compound selected from the group consisting of polyfunctional cyanate esters, prepolymers of said cyanate esters, coprepolymers of said cyanate esters and an amine and mixtures thereof, (b) at least one diene-type rubber and optionally (c) at least one compound selected from the group consisting of polyfunctional maleimides, prepolymers of the maleimides or coprepolymers of the maleimides and an amine is formed on a plastic substrate is disclosed.

## Claims

### Claim 1

A plastic article for electroless plating in which a semi-cured or cured product of a curable resin composition comprises:
(a) at least one cyanate ester compound selected from the group consisting of
(1) a polyfunctional cyanate ester monomer,
(2) a homoprepolymer of one or more cyanate esters of (1), and
(3) a coprepolymer of (1) and an amine, and
(b) at least one diene-type rubber, said composition including a mixture of components (a) and (b), a preliminary reaction product of components (a) and (b), or the combination of said mixture and said preliminary reaction product, is formed on a plastic substrate.

### Claim 2 (depends on 1)

The plastic article as defined in claim 1 wherein the cyanate ester is selected from the group consisting of 1,3-, 1,4-dicyanatobenzene; 1,3,5-tricyanatobenzene; 1,3-, 1,4-, 1,6-, 1,8-, 2,6- or 2,7-dicyanatonaphthalene; 1,3,6-tricyanatonaphthalene; 4,4'-dicyanatobiphenyl; bis(4-cyanatophenyl)-methane; 2-2-bis(4-cyanatophenyl)propane, 2,2-bis(3,5-dichloro-4-cyanatophenyl)propane, 2,2-bis(3,5-dibromo-4-cyanatophenyl)-propane; bis(4-cyanatophenyl)ether; bis(4-cyanatophenyl)-thioether; bis(4-cyanatophenyl)sulfone; tris(4-cyanatophenyl)-phosphite; tris(4-cyanatophenyl)phosphate; bis(3-chloro-4-cyanatophenyl)methane; cyanated novolak; derived from novolak cyanated bisphenol type polycarbonate oligomer derived from bisphenol type polycarbonate oligomer and mixture thereof.

### Claim 3 (depends on 1)

The plastic article as defined in claim 1 wherein component (b) is selected from the group consisting of natural rubbers, butadiene rubber, chloroprene rubber, isoprene rubber, butadiene-acrylonitrile copolymer, butadieneacrylonitrile-isoprene terpolymer, butadiene-styrene copolymer, anionic block copolymer of butadiene and styrene, polybutadiene, butadiene-acrylonitrile copolymer having hydroxyl group or carboxyl group at its end position, and lower molecular polybutadiene, lower molecular polyisoprene, lower molecular polychloroprene and thermal decomposed natural rubbers not having any functional group at its end position.

### Claim 4 (depends on 1)

The plastic article as defined in claim 1 wherein the ratio by weight of component (a) to component (b) is between 99:1 to 1:99.

### Claim 5 (depends on 1)

The plastic article as defined in claim 1 wherein the ratio by weight of component (a) to component (b) is between 95:5 to 20:80.

### Claim 6 (depends on 1)

The plastic article as defined in claim 1 wherein the plastic substrate is reinforced or non-reinforced.

### Claim 7 (depends on 1)

The plastic article as defined in claim 1 wherein the material of the plastic substrate is selected from the group consisting of phenol resin, melamine resin, epoxy resin, unsaturated polyester resin, isocyanate resin, diallyl phthalate resin, silicone resin, acrylic resin, alkyd resin, 1,2-polybutadiene resin, cyanate resin, polyimide resin, resins modified from these resins, polyimide, polyamideimide, polyhydantoin resin, polyparabanic acid, polyphenylenesulfide, crosslinked network polyethylene, nylon, polyphenylene ether, polycarbonate, and polysulfone.

### Claim 8

A plastic article for electroless plating in which a semi-cured or cured product of a curable resin composition comprises:
(a) at least one cyanate ester compound selected from the group consisting of
(1) a polyfunctional cyanate ester monomer,
(2) a homoprepolymer of one or more cyanate esters of (1), and
(3) a coprepolymer of (1) and an amine,
(b) at least one diene-type rubber, and
(c) at least one maleimide compound selected from the group consisting of:
(1) a polyfunctional maleimide,
(2) a homoprepolymer of one or more maleimides of (1), and
(3) a coprepolymer of (1) and an amine,
said composition including a mixture of components (a), (b) and (c), a preliminary reaction product of components (a), (b) and (c), the combination of said mixture and said preliminary reaction product, the combination of (a) and the preliminary reaction product of (b) and (c), the combination of (b) and the preliminary reaction product of (a) and (c), or the combination of (c) and the preliminary reaction product of (a) and (b), is formed on a plastic substrate.

### Claim 9 (depends on 8)

The plastic article as defined in claim 8 wherein the cyanate ester is selected from the group consisting of 1,3-, 1,4-dicyanatobenzene; 1,3,5-tricyanatobenzene; 1,3-, 1,4-, 1,6-, 1,8-, 2,6- or 2,7-dicyanatonaphthalene; 1,3,6-tricyanatonaphthalene; 4,4'-dicyanatobiphenyl; bis(4-cyanatophenyl)methane; 2,2-bis(4-cyanatophenyl)propane, 2,2-bis(3,5-dichloro-4-cyanatophenyl)propane, 2,2-bis(3,5-dibromo-4-cyanatophenyl)propane; bis(4-cyanatophenyl)ether; bis(4-cyanatophenyl)thioether; bis(4-cyanatophenyl)sulfone; tris(4-cyanatophenyl)phosphite; tris(4-cyanatophenyl)phosphate; bis(3-chloro-4-cyanatophenyl)methane; cyanated novolak derived from novolak; cyanated bisphenol type polycarbonate oligomer derived from bisphenol type polycarbonate oligomer and mixture thereof.

### Claim 10 (depends on 8)

The plastic article as defined in claim 8 wherein component (b) is selected from the group consisting of natural rubbers, butadiene rubber, chloroprene rubber, isoprene rubber, butadiene-acrylonitrile copolymer, butadieneacrylonitrile-isoprene terpolymer, butadiene-styrene copolymer, anionic block copolymer of butadiene and styrene, polybutadiene butadiene-acrylonitrile copolymer having hydroxyl group or carboxyl group at its end position, and lower molecular polybutadiene, lower molecular polyisoprene, lower molecular polychloroprene and thermal decomposed natural rubbers not having any functional group at its end position.

### Claim 11 (depends on 8)

The plastic article as defined in claim 8 wherein the plastic substrate is reinforced or non-reinforced.

### Claim 12 (depends on 8)

The plastic article as defined in claim 8 wherein the material of the plastic substrate is selected from the group consisting of phenol resin, melamine resin, epoxy resin, unsaturated polyester resin, isocyanate resin, diallyl phthalate resin, silicone resin, acrylic resin, alkyd resin, 1,2-polybutadiene resin, cyanate resin, polyimide resin, resins modified from these resins, polyimide, polyamideimide, polyhydantoin resin, polyparabanic acid polyphenylenesulfide-crosslinked network polyethylene, nylon, polyphenylene ether, polycarbonate, and polysulfone.

### Claim 13 (depends on 8)

The plastic article as defined in claim 8 wherein the polyfunctional maleimide is selected from the group consisting of 1,3- or 1,4-dimaleimido benzene, 1,3- or 1,4-bis(maleimidomethylene)benzene, 1,3- or 1,4-dimaleimido cyclohexane, 1,3- or 1,4-bis(maleimidomethylene)cyclohexane, 4,4'-dimaleimido biphenyl, bis(4-maleimidophenyl)methane, bis(4-maleimidophenyl)ether, bis(4-maleimidophenyl)sulfone, bis(4-maleimido-3-methylphenyl)methane, bis(4-maleimido-3-chlorophenyl)methane, bis(4-maleimido-3,5-dimethylphenyl)methane, 2,2-bis(4-maleimido-3-methylphenyl)propane, 2,2-bis(4-maleimido-3,5-dibromophenyl)propane, bis(4-maleimidophenyl)-phenylmethane, 3,4-dimaleimidophenyl-4'-maleimidophenylmethane, 1,1-bis(4-maleimidophenyl)-1-phenyl-methane, and maleimido derived from melamine, and maleimide derived from addition product of formalin and an aniline in which benzene rings of two or more aniline bond through methylene group.