IP Library Granted Patent US 8,703,847
Granted Patent B2
US 8,703,847 · App. 13/524,741 · Granted Apr 22, 2014

Glyoxalation of vinylamide polymer

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Quick Facts
Patent No.
US 8,703,847
App. No.
13/524,741
Granted
Apr 22, 2014
Kind
B2
Abstract

The present invention is directed to a method for preparing a cellulose reactive adduct of polyvinylamide and a composition resulting from the method. The preparation of the cellulose reactive adduct is carried out close to a Critical Concentration defined herein. When the reaction is run close to this Critical Concentration, the risk of gelation is minimized, consumed glyoxal is maximized, and shelf live is enhanced. Additionally, the glyoxalated vinylamides of the present invention impart improved wet and dry strengthening efficiency to paper and paperboard when compared to adducts disclosed in previously described art.

Claims (27)

1. A method for preparing a cellulose reactive functionalized polyvinylamide adduct comprising

reacting a substantially aqueous reaction mixture comprising a vinylamide polymer and a cellulose reactive agent to form the adduct,

wherein the vinylamide polymer has an average molecular weight ranging from 70,000 to 500,000 Daltons and the concentration of the vinylamide polymer is less than about 4 weight percent of the reaction mixture at any stage during the adduct reaction, and

the adduct is characterized by a viscosity of no more than 30 centipoise measured using a BROOKFIELD viscometer at a speed of 60 rpm and a temperature of 25° C.

2. A method for preparing a cellulose reactive functionalized polyvinylamide adduct comprising

reacting a substantially aqueous reaction mixture comprising a vinylamide polymer and a cellulose reactive agent to form the adduct,

wherein a molar ratio of amide to cellulose reactive agent is in the range of about 2:1 to about 12:1, wherein the reaction mixture has a pre-reaction viscosity and a second viscosity and the second viscosity is measured once the reaction has progressed to a point where at least 50 wt. % of the total cellulose reactive agent has been consumed, and a difference between the pre-reaction and second viscosities is characterized by a viscosity decrease, no change in viscosity, or an increase of less than about 50% of the pre-reaction viscosity.

3. A Water-soluble glyoxalated-polyvinylamide thermosetting resin obtained by the method according to claim 1 .

4. The method according to claim 1 , wherein the cellulose reactive agent comprises more than one aldehyde functionality.

5. The method according to claim 1 , wherein the cellulose reactive agent is selected from the group consisting of glyoxal, glutaraldehyde, furan dialdehyde, 2-hydroxyadipaldehyde, succinaldehyde, dialdehyde starch, diepoxy compounds, and combinations thereof.

6. The method according to claim 1 , which further contains, in addition to the vinylamide polymer, a cationic polymer.

7. A paper or board incorporating the adduct obtained by the method according to claim 1 .

8. A substantially aqueous glyoxalated-polyvinylamide thermosetting polymer composition, said composition comprising

a reaction product of a vinylamide polymer and glyoxal, wherein said composition contains substantially no organic liquid,

wherein the vinylamide polymer has an average molecular weight ranging from 70,000 to 500,000 Daltons and has a concentration ranging from about 0.1 to less than 4 wt. % based on the composition, and

the reaction product is characterized by a viscosity of no more than 30 centipoise measured using a BROOKFIELD viscometer at a speed of 60 rpm and a temperature of 25° C.

9. The substantially aqueous glyoxalated-polyvinylamide thermosetting polymer composition according to claim 8 , wherein a molar ratio of the amide functionality on the vinylamide polymer and glyoxal is between about 2 to 1 and about 12 to 1.

10. The substantially aqueous glyoxalated-polyvinylamide thermosetting polymer composition of claim 8 , wherein the vinylamide polymer has an average molecular weight ranging from 75,000 to 500,000.

11. The substantially aqueous glyoxalated-polyvinylamide thermosetting polymer composition of claim 8 , wherein the concentration of the vinylamide polymer ranges from about 0.5 to about 3%.

12. The substantially aqueous glyoxalated-polyvinylamide thermosetting polymer composition according to claim 8 , which further includes a second polymer in addition to the glyoxalated-polyvinylamide.

13. The substantially aqueous glyoxalated-polyvinylamide thermosetting polymer composition of claim 8 , wherein the vinylamide polymer is a homopolymer or copolymer formed from (meth)acrylamide or a substituted (meth)acrylamide.

14. The substantially aqueous glyoxalated-polyvinylamide thermosetting polymer composition of claim 8 , wherein the vinylamide polymer is nonionic, cationic, potentially cationic, anionic, potentially anionic or amphoteric, or combinations thereof.

15. The substantially aqueous glyoxalated-polyvinylamide thermosetting polymer composition of claim 8 , wherein the vinylamide polymer is cationic and is formed from a monomer or potentially cationic monomer,

which cationic monomer is selected from the group consisting of diallyldialkyl amines, (dialkylamino)alkyl (meth) acrylates, 2-vinylpyridines, (dialkylamino alkyl(meth) acrylamides, (p-vinylphenyl)-trimethylammonium chloride, and 1-methacryloyl-4-methyl piperazine including acid addition and quaternary ammonium salts thereof.

16. The substantially aqueous glyoxalated-polyvinylamide thermosetting polymer composition of claim 8 , wherein the vinylamide polymer is formed from about 0.1 to about 40 weight percent of the (meth)acrylamide or a substituted (meth)acrylamide monomer.

17. The substantially aqueous glyoxalated-polyvinylamide thermosetting polymer composition of claim 8 , wherein the vinylamide polymer is linear, crosslinked, chain-transferred, or crosslinked and chain-transferred.

18. The substantially aqueous glyoxalated-polyvinylamide thermosetting polymer composition of claim 8 , wherein the vinylamide polymer is crosslinked using at least a difunctional monomer selected from the group consisting of methylene bis(meth)acrylamide; triallylammonium chloride; tetraallyl ammonium chloride; polyethyleneglycol diacrylate; polyethyleneglycol dimethacrylate; N-vinyl acrylamide; divinylbenzene; tetra (ethyleneglycol) diacrylate; dimethylallylaminoethylacrylate ammonium chloride; sodium salt of diallyloxyacetic acid; diallyloctylamide; trimethyllpropane ethoxylate triacryalte; N-allylacrylamide; N-methylailylacrylamide; pentaerythritol triacrylate, and combinations thereof.

Assignments (14)
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 →
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 →
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 (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 →
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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2020
From: BASF SE
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 054735/0659 →
ASSET TRANSFER AGREEMENT Recorded Mar 6, 2014
From: CIBA CORPORATION
To: BASF SE
Reel/Frame 032399/0377 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 6, 2014
From: WRIGHT, MATTHEW D.
To: CIBA SPECIALTY CHEMICALS CORPORATION
Reel/Frame 032367/0430 →
CHANGE OF NAME Recorded Mar 6, 2014
From: CIBA SPECIALTY CHEMICALS CORPORATION
To: CIBA CORPORATION
Reel/Frame 032367/0475 →