IP Library Granted Patent US 10,219,391
Granted Patent B2
US 10,219,391 · App. 15/285,752 · Granted Feb 26, 2019

Solution and process for the pre-treatment of copper surfaces using an N-alkoxylated adhesion-promoting compound

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Quick Facts
Patent No.
US 10,219,391
App. No.
15/285,752
Granted
Feb 26, 2019
Kind
B2
Abstract

A method for pretreating a copper surface for the subsequent formation of a firmly adhesive bond between the copper surface and a plastic material substrate. The method comprises bringing a copper surface into contact with: a) hydrogen peroxide; b) an acid; c) a nitrogen-containing, five-membered, heterocyclic compound; and d) a lactam, amide, or polyamide, connected at one or more of its nitrogen atoms with at least one residue of formula (I), wherein: n is an integer from 1 to 100; R 1 is hydrogen or a hydrocarbon residue with 1 to 6 carbon atoms; R 2 is hydrogen or a hydrocarbon residue with 1 to 6 carbon atoms; and each R 1 and R 2 in a —(CHR 1 —CHR 2 —O)— moiety is selected independently of each R 1 and R 2 in another —(CHR 1 —CHR 2 —O)— moiety.

Claims (36)

1. A method for pre-treating a copper surface, the method comprising:

(A) contacting the copper surface with a first solution comprising:

a) hydrogen peroxide;

b) an acid; and

c) a nitrogen-containing, five-membered, heterocyclic compound; and

(B) contacting the copper surface with a second solution comprising a nitrogen-containing, adhesion-promoting compound selected from a lactam, amide or polyamide and that is connected at one or more of its nitrogen atoms with at least one residue of formula (I)

wherein:

n is an integer from 1 to 100;

R 1 is hydrogen or a hydrocarbon residue with 1 to 6 carbon atoms;

R 2 is hydrogen or a hydrocarbon residue with 1 to 6 carbon atoms; and

each R 1 and R 2 in a —(CHR 1 —CHR 2 —O)— moiety is selected independently of each R 1 and R 2 in another —(CHR 1 —CHR 2 —O)— moiety.

2. The method of claim 1 , wherein the nitrogen-containing, adhesion-promoting compound is a compound of formula (II)

wherein:

n is an integer from 1 to 100;

R 1 is hydrogen or a hydrocarbon residue with 1 to 6 carbon atoms;

R 2 is hydrogen or a hydrocarbon residue with 1 to 6 carbon atoms;

each R 1 and R 2 in a —(CHR 1 —CHR 2 —O)— moiety is selected independently of each R 1 and R 2 in another —(CHR 1 —CHR 2 —O)— moiety; and

R 3 is a hydrocarbon residue with 1 to 20 carbon atoms.

3. The method of claim 1 , wherein the nitrogen-containing, adhesion-promoting compound is a compound of formula (III)

wherein:

x is the number of repeating monomer units;

n is an integer from 1 to 100, and each n in a —(CHR 1 —CHR 2 —O) n — moiety or chain is selected independently of each n in another —(CHR 1 —CHR 2 —O) n — moiety or chain;

R 1 is hydrogen or a hydrocarbon residue with 1 to 6 carbon atoms;

R 2 is hydrogen or a hydrocarbon residue with 1 to 6 carbon atoms;

each R 1 and R in a —(CHR 1 —CHR 2 —O)— moiety is selected independently of each R 1 and R 2 in another —(CHR 1 —CHR 2 —O)— moiety; and

R 3 is a hydrocarbon residue with 1 to 20 carbon atoms, and each R 1 in a —(N—R 3 —CO)— moiety is selected independently of each R 3 in another —(N—R 3 —CO)— moiety.

4. The method of claim 1 , wherein the second solution further comprises a compound selected from sulphinic acid, selenic acid, telluric acid, a heterocyclic compound that comprises at least one sulphur, selenium and/or tellurium atom in the heterocycle, or salt of formula (VIII)

wherein:

A is sulfur, selenium, or tellurium;

R 9 , R 10 , and R 11 are each independently alkyl, substituted alkyl, alkenyl, phenyl, substituted phenyl, benzyl, cycloalkyl, or substituted cycloalkyl; and

Z − is an anion of an inorganic or organic acid or hydroxide;

wherein:

the acid of the first solution is different than the sulphinic, selenic or telluric acids selected for the second solution, and

the nitrogen-containing, five-membered, heterocyclic compound of the first solution contains no sulphur atom, selenium atom or tellurium atom in the heterocycle.

5. The method of claim 2 , wherein R 3 is —(CH 2 ) y — and y is an integer from 2 to 12.

6. The method of claim 3 , wherein R 3 is —(CH 2 ) y — and y is an integer from 2 to 12.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Aug 18, 2022
From: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
To: ATOTECH DEUTSCHLAND GMBH & CO. KG (F/K/A ATOTECH DEUTSCHLAND GMBH); ATOTECH USA, LLC
Reel/Frame 061521/0103 →
SECURITY INTEREST Recorded Mar 18, 2021
From: ATOTECH DEUTSCHLAND GMBH; ATOTECH USA, LLC
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 055650/0093 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 11, 2016
From: SPARING, CHRISTIAN; HUELSMANN, THOMAS; CLICQUE, ARNO; BROOKS, PATRICK; ZEE, ADRIAN; BRUNNER, HEIKO
To: ATOTECH DEUTSCHLAND GMBH
Reel/Frame 039983/0758 →