IP Library Granted Patent US 8,691,987
Granted Patent B2
US 8,691,987 · App. 12/890,013 · Granted Apr 8, 2014

Method of producing polymeric phenazonium compounds

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Quick Facts
Patent No.
US 8,691,987
App. No.
12/890,013
Granted
Apr 8, 2014
Kind
B2
Abstract

A process of making a polymeric phenazonium compound having the general formula: wherein R 1 , R 2 , R 4 , R 5 , R 6 , R 8 and R 9 are the same or different, and represent hydrogen, a low alkyl or a substituted aryl, R 3 starts with NH 2 and is diazotized followed by polymerization, R 5 and R 8 may alternatively represent monomeric or polymeric phenazonium radicals, R 7 with its substituent group is a substituted amine, with R X and R Y representing any combination of CH 3 , C 2 H 5 , and hydrogen, except that R X and R Y cannot both be hydrogen, A is an acid radical, and n is an integer from 2 to 100, preferably from 2 to 20 is described. The polymeric phenazonium compound is usable in as an additive in a metal plating bath. The method includes the steps of: a) dissolving an effective amount of an amino compound in a formic acid solution; b) adding a nitrite salt to diazotize the amino compound; and c) adding sulfamic acid to neutralize any excess nitrous acid that may be formed in step b), whereby a polymeric phenazonium compound is produced.

Claims (12)

1. A process for making a polymeric phenazonium compound and using said compound in a plating bath, said process comprising:

(a) dissolving an effective amount of an amino compound in a formic acid solution;

(b) adding a nitrite salt to diazotize the amino compound; and

(c) adding sulfamic acid to neutralize any excess nitrous acid that may be formed in step b);

whereby a polymeric phenazonium compound is produced;

wherein the amino compound comprises an amino compound selected from the group consisting of 2-methyl-3-amino-7-dimethylamino-5-phenyl-phenazonium sulfate, 3-amino-6-methyl-7-dimethylamino-5-phenyl-phenazonium hydrogen sulfate, 2-methyl-3-amino-7-diethylamino-5-phenyl-phenazonium chloride, 3-amno-dimethylamino-5-methyl hydrogen sulfate, 2-methyl-3-amino-7-dimethylamino-phenazonium hydrogen sulfate, 3-amino-7-methlamno-5-phenylphenazonium acetate, 2-phenyl-3-amino-7-ethylamino-5-phenyl-phenazonium chloride, 1,2,6,9-tetrametyl-3-amno-7-diethylamino-5-phenylphenazonium hydrogen sulfate, 2-8-dimethyl-3-amino-7-diethylamino-5-phenyl-phenazonium hydrogen sulfate, 2,8-dimethyl-3-amino-7-diethylamino-5-tolyl-phenazonium chloride, and 2,9-diphenyl-3-amino-6-metyl-7-dimethylamino-5-phenyl-phenazonium hydrogen sulfate;

(d) adding said polymeric phenazonium compound to a plating bath.

2. The process of claim 1 , wherein the nitrite salt is sodium nitrite.

3. The process according to claim 1 , wherein the amino compound is dissolved in the formic acid at a temperature of between about −10 about 0° C.

4. The process according to claim 1 , wherein the concentration of the amino compound in the formic acid solution is between about 100 g/l and about 200 g/l.

5. The process according to claim 1 , wherein the concentration of the amino compound in the formic acid solution is between about 120 g/l and about 185 g/l.

6. The process according to claim 1 , wherein the process of producing the polymeric phenazonium compound does not include a step of neutralizing the polymeric phenazonium compound with a base.

Assignments (7)
ASSIGNMENT OF SECURITY INTEREST IN PATENT COLLATERAL Recorded Nov 17, 2022
From: BARCLAYS BANK PLC
To: CITIBANK, N.A.
Reel/Frame 061956/0643 →
SECURITY INTEREST Recorded Feb 5, 2019
From: MACDERMID ACUMEN, INC.
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 048260/0828 →
RELEASE OF SECURITY INTEREST Recorded Feb 4, 2019
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: MACDERMID ACUMEN, INC.
Reel/Frame 048232/0405 →
ASSIGNMENT AND ASSUMPTION OF SECURITY INTERESTS AT REEL/FRAME NOS. 30831/0549, 30833/0660, 30831/0606, 30833/0700, AND 30833/0727 Recorded Nov 1, 2013
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS FIRST LIEN COLLATERAL AGENT
To: BARCLAYS BANK PLC, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 031536/0778 →
RELEASE OF SECURITY INTEREST IN PATENT COLLATERAL AT REEL/FRAME NO. 30831/0675 Recorded Nov 1, 2013
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS SECOND LIEN COLLATERAL AGENT
To: MACDERMID ACUMEN, INC.
Reel/Frame 031537/0094 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded Jul 19, 2013
From: MACDERMID ACUMEN, INC.
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS FIRST LIEN COLLATERAL AGENT
Reel/Frame 030831/0549 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded Jul 19, 2013
From: MACDERMID ACUMEN, INC.
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 030831/0675 →