# US 9,518,324 B2 · Copolymers of diglycidyl ether terminated polysiloxane compounds and non-aromatic polyamines

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- Number: US 9,518,324 B2
- Document ID: US9518324B2
- Status: Granted
- Kind: B2
- Application number: 14/971,284
- Filed: 2015-12-16
- Published: 2016-04-14
- Granted: 2016-12-13
- Earliest claimed: 2014-05-26
- Assignees: Rohm and Haas Electronic Materials LLC
- Applicants: Rohm and Haas Electronic Materials LLC
- Inventors: Julia Kozhukh; Zuhra I. Niazimbetova; Kristen M. Milum
- Web page: https://patentgrep.com/patent/US9518324B2

## CPC

- C23C 18/31: Coating with metals
- C08G 77/388: containing nitrogen
- C08L 83/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C09D 183/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
- C09D 183/14: in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C09D183/10 takes precedence)
- C23C 18/18: Pretreatment of the material to be coated
- G03F 7/0751: {used as adhesion-promoting additives or as means to improve adhesion}
- H05K 1/03: Use of materials for the substrate
- H05K 3/181: {by electroless plating (adhesives therefor H05K3/387)}
- H05K 3/422: {characterised by electroless plating method; pretreatment therefor}
- H05K 3/427: {initial plating of through-holes in metal-clad substrates}
- H05K 2201/09581: Applying an insulating coating on the walls of holes
- 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)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- H05K: PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS

## Abstract

Copolymers of diglycidyl ether terminated polysiloxane compounds and non-aromatic polyamines are used in the preparation of dielectric materials for electroless metal plating. The copolymers may be used in the manufacture of printed circuit boards such as in cleaning and conditioning through-holes prior to electroless metallization.

## Claims

### Claim 1

A method comprising:
a) providing a substrate comprising a dielectric;
b) contacting the substrate with a composition comprising a reaction product of one or more diglycidyl ether terminated polysiloxane compounds and one or more non-aromatic polyamines;
c) applying a catalyst to the substrate and
d) electrolessly plating metal on the substrate with an electroless metal plating bath.

### Claim 2 (depends on 1)

The method of claim 1, wherein the catalyst is an ionic catalyst.

### Claim 3 (depends on 1)

The method of claim 1, wherein the substrate further comprises a plurality of through-holes, vias or combinations thereof.

### Claim 4 (depends on 1)

The method of claim 1, wherein the one or more diglycidyl ether terminated compounds have a formula:
wherein R1, R2, R3, R4, R5 and R6 may be the same or different and are chosen from hydrogen; linear or branched, substituted or unsubstituted (C1-C6)alkyl; m is an integer of 1 to 6, and n is an integer of 1 to 20.

### Claim 5 (depends on 1)

The method of claim 1, wherein the one or more non-aromatic polyamines are chosen from aliphatic polyamines and alicyclic polyamines.

### Claim 6 (depends on 1)

The method of claim 1, wherein the one or more non-aromatic polyamines comprises a formula:
wherein R7, R8 and R9 are independently chosen from hydrogen; linear or branched, substituted or unsubstituted (C1-C10)alkylamine; linear or branched, substituted or unsubstituted (C1-C10)alkyl; a moiety having a general formula:
wherein R10 to R15 are independently chosen from hydrogen; linear or branched, substituted or unsubstituted (C1-C10)alkyl; linear or branched, substituted or unsubstituted (C1-C10)alkylamine; and with the proviso that if the nitrogen atoms in compounds II and III are tertiary, at least one of R7, R8, and R9 comprises substituent groups with two or more primary nitrogen atoms, secondary nitrogen atoms, or a combination of primary and secondary nitrogen atoms; and q, r and t may be the same or different and are integers of 1 to 10.

### Claim 7 (depends on 1)

The method of claim 1, wherein the catalyst is a tin-palladium colloidal catalyst.

### Claim 8 (depends on 1)

The method of claim 1, wherein the composition further comprises one or more additives chosen from water miscible organic solvents, surfactants, complexing agents and one or more pH adjusting agents.

### Claim 9 (depends on 1)

The method of claim 1, wherein the electroless metal plating bath is chosen from a copper, copper alloy, nickel and nickel alloy electroless metal plating bath.