IP Library Granted Patent US 8,518,215
Granted Patent B2
US 8,518,215 · App. 12/696,237 · Granted Aug 27, 2013

Quaternary vinylamine-containing polymers as additives in papermaking

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Quick Facts
Patent No.
US 8,518,215
App. No.
12/696,237
Granted
Aug 27, 2013
Kind
B2
Abstract

Vinylamine-containing polymers are disclosed where the amine groups are substituted with cationic functional groups. Processes for preparing such polymers, as well as compositions comprising such polymers are also disclosed. Among other applications, these polymers can be used in papermaking applications as dry strength additives, wet strength additives, retention aids, drainage aids, and pitch and stickies control agents.

Claims (25)

1. A method of making paper providing improved strength and optionally retention and drainage and fixative properties, the method comprising the step of adding from 0.05 to 2.0 wt percent of a polymer based on the dry weight of pulp to the wet end of a paper machine, the polymer comprising randomly distributed repeating monomer units having at least one of the formulae (I) and (II):

wherein

X − is an anion;

R 1 is a straight chain or branched alkyl group containing up to 12 carbons, optionally substituted with hydroxyl;

R 2 and R 3 , identically or differently are H or a straight chain or branched alkyl containing up to 22 carbons;

R 4 is H or a straight chain or branched alkyl containing up to 22 carbons;

n 1 , and n 2 independently may be 0 mole percent;

wherein the sum of n 1 and n 2 is greater than 0.1 mole percent and less than 20 mole percent; and wherein said polymer has a molecular weight in the range of from about 20,000 to about 800,000 Daltons.

2. The method of claim 1 wherein the polymer further comprising randomly distributed repeating monomer units having at least one of the formulae (III), (IV), (V), (VI), (VII), and (VIII):

wherein

R 5 and R 6 identically or differently are H, straight chain or branched alkyl containing up to 22 carbons, —COOH, —COOR 2 , —CH 2 CO 2 H, —CH 2 CO 2 R 2 , —CH 2 NR 2 R 3 , —NR 2 R 3 , —CONR 1 R 4 , —OH, —OCOR 2 , —OR 2 , —NO 2 , N + (CH 3 ) 3 , alkenyl, alkynyl, or alkanoxyl; and

m 1 , m 2 , m 3 , m 4 , m 6 , and m 6 represent the mole fraction of formula III, IV, V, VI, VII and VIII respectively in the polymer.

3. The method of claim 1 , wherein R 1 is —CH 2 CH(OH)CH 2 —.

4. The method of claim 3 , wherein R 2 and R 3 are —CH 3 and the sum of n 1 and n 2 is in the range of from 2 to 20 mole percent.

5. The method of claim 1 , wherein R 1 is —CH 2 CH 2 —.

6. The method of claim 1 , wherein R 1 is —CH 2 CH 2 CH 3 — and the sum of n 1 and n 2 is in the range of from 2 to 20 mole percent.

7. The method of claim 1 , wherein the sum of n 1 and n 2 is in the range of from 3 to 20 mole percent.

8. The method of claim 1 , wherein said polymer has a molecular weight in the range of from about 75,000 to about 600,000 Daltons.

9. The method of claim 3 , wherein the sum of n 1 and n 2 is in the range of from 3 to 20 mole percent.

10. The method of claim 1 , wherein said polymer has a positive charge density of at least 5.0 meq/g at pH 7.0.

11. The method of claim 1 , wherein said polymer has a positive charge density of at least 7.0 meq/g at pH 7.0.

12. The method of claim 1 , wherein R 1 is —CH 2 CH(OH)CH 2 —, wherein R 2 and R 3 are —CH 3 , the sum of n 1 and n 2 is in the range of from 3 to 20 mole percent, the polymer has a molecular weight in the range of from about 75,000 to about 600,000 Daltons, and the polymer has a positive charge density of at least 5.0 meq/g at pH 7.0.

13. The method of claim 12 wherein the polymer has a positive charge density of at least 7.0 meq/g at pH 7.0.

14. The method of claim 1 , wherein R 1 is —CH 2 CH 2 —, wherein R 2 and R 3 are —CH 3 , the sum of n 1 and n 2 is in the range of from 3 to 20 mole percent, the polymer has a molecular weight in the range of from about 75,000 to about 600,000 Daltons, and the polymer has a positive charge density of at least 5.0 meq/g at pH 7.0.

15. The polymer of claim 1 , wherein the sum of n 1 and n 2 is between 0.1 mole percent to less than 10 mole percent.

Assignments (24)
SECURITY INTEREST Recorded Nov 14, 2025
From: CHEM-AQUA, INC.; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; NCH CORPORATION; NCH LIFE SCIENCES LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 073570/0838 →
RELEASE OF SECURITY INTEREST Recorded Nov 14, 2025
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
To: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 073564/0864 →
RELEASE OF 2023 NOTES PATENT SECURITY INTERESTS Recorded Oct 10, 2025
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 073074/0198 →
SECURITY AGREEMENT (NOTES) Recorded Oct 10, 2025
From: DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 073061/0885 →
SECURITY AGREEMENT (2024 NOTES) Recorded Jun 24, 2024
From: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 067824/0278 →
2023 NOTES PATENT SECURITY AGREEMENT Recorded Jul 7, 2023
From: BIRKO CORPORATION; SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE GLOBAL CORPORATION
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
Reel/Frame 064225/0170 →
SECURITY AGREEMENT (NOTES) Recorded Sep 14, 2022
From: SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
Reel/Frame 061432/0821 →
RELEASE OF SECURITY INTEREST Recorded Nov 10, 2021
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 058856/0724 →
ABL PATENT SECURITY AGREEMENT Recorded Nov 10, 2021
From: INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: BANK OF AMERICA, N.A.
Reel/Frame 058102/0122 →
TERM LOAN PATENT SECURITY AGREEMENT Recorded Nov 10, 2021
From: INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: GOLDMAN SACHS BANK USA
Reel/Frame 058102/0407 →
NOTES SECURITY AGREEMENT Recorded Nov 10, 2021
From: INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
Reel/Frame 058103/0066 →
RELEASE OF SECURITY INTEREST Recorded Nov 10, 2021
From: CITIBANK, N.A.
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 058848/0636 →
SECOND LIEN NOTICE AND CONFIRMATION OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Jul 20, 2018
From: SOLENIS TECHNOLOGIES, L.P.
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 046629/0213 →
INTELLECTUAL PROPERTY FIRST LIEN SECURITY AGREEMENT RELEASE Recorded Jul 20, 2018
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 046594/0252 →
INTELLECTUAL PROPERTY SECOND LIEN SECURITY AGREEMENT RELEASE Recorded Jul 20, 2018
From: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 047058/0800 →
FIRST LIEN NOTICE AND CONFIRMATION OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Jul 20, 2018
From: SOLENIS TECHNOLOGIES, L.P.
To: CITIBANK, N.A., COLLATERAL AGENT
Reel/Frame 046595/0241 →
NOTICE AND CONFIRMATION OF GRANT OF SECURITY INTEREST IN PATENTS (SECOND LIEN) Recorded Aug 14, 2014
From: SOLENIS TECHNOLOGIES, L.P.
To: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
Reel/Frame 033535/0847 →
NOTICE AND CONFIRMATION OF GRANT OF SECURITY INTEREST IN PATENTS (FIRST LIEN) Recorded Aug 14, 2014
From: SOLENIS TECHNOLOGIES, L.P.
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 033535/0806 →
U.S. ASSIGNMENT OF PATENTS Recorded Aug 4, 2014
From: HERCULES INCORPORATED
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 033470/0922 →
RELEASE OF PATENT SECURITY AGREEMENT Recorded Mar 18, 2013
From: THE BANK OF NOVA SCOTIA
To: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; ISP INVESTMENTS INC.; HERCULES INCORPORATED
Reel/Frame 030025/0320 →
SECURITY AGREEMENT Recorded Sep 16, 2011
From: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; HERCULES INCORPORATED; AQUALON COMPANY; ISP INVESTMENT INC.
To: THE BANK OF NOVA SCOTIA, AS ADMINISTRATIVE AGENT
Reel/Frame 026918/0052 →
RELEASE OF PATENT SECURITY AGREEMENT Recorded Sep 15, 2011
From: BANK OF AMERICA, N.A.
To: ASHLAND, INC.; ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; HERCULES INCORPORATED
Reel/Frame 026927/0247 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 18, 2010
From: MCKAY, JONATHAN M; GU, QU-MING; RIEHLE, RICHARD J
To: HERCULES INCORPORATED
Reel/Frame 025371/0445 →
SECURITY AGREEMENT Recorded Apr 14, 2010
From: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; HERCULES INCORPORATED
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 024225/0289 →