IP Library Granted Patent US 8,614,279
Granted Patent B2
US 8,614,279 · App. 13/446,486 · Granted Dec 24, 2013

Process to produce an acylated vinylamine-containing polymer and its application as a papermaking additive

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Quick Facts
Patent No.
US 8,614,279
App. No.
13/446,486
Granted
Dec 24, 2013
Kind
B2
Abstract

A process for producing an acylated vinylamine-containing polymer is disclosed. The acylated vinylamine-containing polymer is produced by reacting a vinylamine-containing polymer with at least one acylating agent.

Claims (18)

1. A process for producing acylated vinylamine-containing polymer comprising the steps of

a. conducting free radical polymerization of N-vinylformamide in an aqueous solution;

b. conducting alkaline hydrolysis to form a polyvinylamine; and

c. reacting the vinylamine-containing polymer with at least one acylating agent,

wherein the acylating agent is selected from the group consisting of acyl anhydride, acyl halide and mixtures thereof; and

wherein acylation temperatures are from about 20° C. to about 50° C. and wherein the acyl anhydride is not a cyclic anhydride.

2. The process of claim 1 wherein at least one vinylamine-containing polymer is selected from the groups consisting of partially or completely hydrolyzed poly(N-vinylformamide), copolymers of N-vinylformamide and vinylamine, copolymers of vinylamine and amidine, copolymers of N-vinylacetamide and vinylamine, terpolymers of N-vinylformamide, vinylamine and amidine, terpolymers of N-vinylformamide, vinylamine and vinylamine methyl chloride quaternary ammonium salts, terpolymers of N-vinylformamide, vinylamine and vinyl alcohol, terpolymers of N-vinylformamide, vinylamine and vinyl acetate, terpolymers of N-vinylformamide, vinylamine and acrylamide, terpolymers of N-vinylformamide, vinylamine and acrylate, terpolymers of N-vinylformamide, vinylamine, and diallyldimethyl ammonium chloride, terpolymers of N-vinylformamide, vinylamine, and vinyl trimethoxysilane, modified vinylamine-containing polymers, or mixtures thereof.

3. The process of claim 1 wherein the vinylamine-containing polymer comprises partially or completely hydrolyzed poly(N-vinylformamide).

4. The process of claim 1 wherein the acylating agent comprises acyl anhydride.

5. The process of claim 1 wherein the acylating agent comprises acyl halide.

6. The process of claim 1 wherein the acylating agent is selected from the group consisting of acetic anhydride, propionic anhydride, butyric anhydride, heptanoic anhydride, benzoic anhydride, phenylacetic anhydride, crotonic anhydride, chloroacetic anhydride, dichloroacetic anhydride and trifloroacetic anhydride, heptanoyl anhydride, an acyl halide and mixtures thereof.

7. The process of claim 1 wherein the acylating agent comprises acetic anhydride.

8. The process of claim 1 wherein the acylating agent is selected from the group consisting of an acyl chloride, acyl bromide, acetyl chloride, propionyl chloride, butyryl chloride, benzoyl chloride, phenylacetyl chloride, crotonyl chloride, chloroacetyl chloride and mixtures thereof.

9. The process of claim 1 wherein the acylated vinylamine-containing polymer has a molecular weight in the range of from about 5,000 to about 2,000,000 Daltons.

10. The process of claim 1 wherein the polyvinylamine and the acylating agent are reacted at a pH of between 7 and 11.

11. The process of claim 1 wherein the polyvinylamine and the acylating agent are reacted at a temperature of between 24-50° C.

12. The process of claim 1 wherein the polyvinylamine and the acylating agent are reacted for a period of between 0.1 and 4 hours.

13. The process of claim 1 wherein the polyvinylamine and the acylating agent are reacted at a pH of between 7 and 11 and at a temperature of between 24-50° C.

Assignments (16)
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 →
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 →
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 →
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 →
RELEASE OF SECURITY INTEREST Recorded Nov 10, 2021
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 058856/0724 →
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 →
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 →
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 →
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 →