IP Library › Granted Patent US 12,421,330
Granted Patent B2
US 12,421,330 · App. 18/873,218 · Granted Sep 23, 2025

Polymer and its preparation method

Inventors: Gatien Faucher (Andrezieux Boutheon, FR); Damien Fougerouse (Andrezieux Boutheon, FR); Cyril Barriere (Andrezieux Boutheon, FR)
Assignee: SNF GROUP
C08F8/28C08F285/00D21H17/37D21H21/18D21H27/10
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Quick Facts
Patent No.
US 12,421,330
App. No.
18/873,218
Granted
Sep 23, 2025
Kind
B2
Abstract

This invention relates to a new water-soluble dialdehyde-functionalized polymer its preparation method and use, notably for application in the field of paper or cardboard manufacturing.

Claims (68)

1. A water-soluble dialdehyde-functionalized polymer comprising

at least one monomer A: cationic or anionic;

at least one monomer B: non-ionic;

at least one structuring system comprising:

(i) at least one compound I, selected from: allylsulfonic acid, methallylsulfonic acid, allyldisulfonic acid, methallyldisulfonic acid, salts and mixtures thereof;

(ii) at least one compound II of formula (1), different from the at least one monomer B:

R 1 and R 2 being, independently of one another, a hydrogen atom or a methyl group, an ethyl group, an isopropyl group or a CH 2 —OH group;

R 1 and R 2 not both being a hydrogen atom;

said polymer being obtained according to the following steps:

a) formation of a solution (S1) comprising at least a first fraction (F1) containing (1) at least one monomer selected from monomers A and B and (2) at least one compound selected from compounds I and II;

b) polymerization 1 (PO1) of the fraction F1 to form a solution of a first gradient polymer (PG1);

c) addition, to the solution comprising PG1, of a second fraction (F2) containing (1) at least one monomer selected from monomers A and B and (2) at least one compound selected from compounds I and II;

d) polymerization 2 (PO2) of the fraction F2 on PG1 in order to form a solution of a second gradient polymer (PG2);

e) addition, to the solution comprising PG2, of a third fraction (F3) containing (1) at least one monomer selected from monomers A and B and (2) at least one compound selected from compounds I and II;

f) polymerization 3 (PO3) of the fraction F3 on PG2, in order to form a solution comprising a base polymer;

g) dilution of the solution comprising the base polymer and reaction between at least one dialdehyde and the base polymer in order to obtain a water-soluble dialdehyde-functionalized polymer;

at least one of the fractions F1, F2 or F3 contains at least one monomer A,

at least one of the fractions F1, F2 or F3 contains at least one monomer B,

at least one of the fractions F1, F2 or F3 contains at least one compound I and

at least one of the fractions F1, F2 or F3 contains at least one compound II;

with monomer A being distinct from a mixture of cationic monomer and anionic monomer,

when monomer A is anionic, the water-soluble dialdehyde-functionalized polymer does not comprise any cationic monomer,

when monomer A is cationic, the water-soluble dialdehyde-functionalized polymer does not comprise any anionic monomer, with the exception of compound I.

2. The water-soluble dialdehyde-functionalized polymer according to claim 1 , wherein at least one of fractions F1, F2 or F3 is different from the other fractions.

3. The water-soluble dialdehyde-functionalized polymer according to claim 1 , wherein the at least one monomer A is cationic.

4. The water-soluble dialdehyde-functionalized polymer according to claim 1 , wherein the at least one monomer A is selected from quaternized dimethylaminoethyl acrylate, quaternized dimethylaminoethyl methacrylate, diallyldimethylammonium chloride, propyltrimethyl ammonium acrylamide chloride, propyltrimethylmethacrylamide ammonium chloride and mixtures thereof, and that the dialdehyde is selected from the group consisting of glyoxal, glutaraldehyde, furane-dialdehyde, adipaldehyde, succinaldehyde, dialdehyde starch, 2,2 dimethoxyethanal, diepoxy compounds, and mixtures thereof.

5. The water-soluble dialdehyde-functionalized polymer according to claim 1 , wherein the at least one non-ionic monomer B is selected from acrylamide, acrylonitrile, methacrylamide and in that the dialdehyde is glyoxal.

6. The water-soluble dialdehyde-functionalized polymer according to claim 1 , wherein it comprises between 500 and 50,000 ppm of compound I, based on to the total weight of monomers A and B;

and wherein it comprises between 500 and 50,000 ppm of compound II, based on to the total weight of monomers A and B.

7. The water-soluble dialdehyde-functionalized polymer according to claim 1 , wherein compound II is selected from: N,N-dimethylacrylamide, N,N-diethylacrylamide, N,N-isopropylacrylamide, N-methylolacrylamide and mixtures thereof.

8. A paper or cardboard manufacturing method comprising adding a water-soluble dialdehyde-functionalized polymer according to claim 1 into an aqueous solution of fibers and forming a sheet of paper or cardboard.

9. A method for recovery of hydrocarbons; drilling or cementing of wells; stimulation of hydrocarbon wells; open-circuit water processing; treatment of fermentation musts; treatment of sludges; in construction; in lumber processing; treatment of hydraulic composition; in the mining industry; formulation of cosmetic products; formulation of detergents; textile manufacturing; in the geothermal sector; manufacture of sanitary napkins; or in agriculture, said method comprising adding a water-soluble dialdehyde-functionalized polymer according to claim 1 into an aqueous solution, and using the resultant solution in said method.

10. A flocculant, coagulant, binding agent, fixing agent, viscosity-reducing agent, thickening agent, absorption agent, friction-reducing agent, drainage agent, charge-retaining agent, dehydrating agent, conditioning agent, stabilizing agent, fixing agent, film-forming agent, sizing agent, superplasticizer agent, clay inhibitor or dispersant, comprising the water-soluble dialdehyde-functionalized polymer according to claim 1 .

11. The water-soluble dialdehyde-functionalized polymer according to claim 2 , wherein the at least one monomer A is cationic.

12. The water-soluble dialdehyde-functionalized polymer according to claim 11 , wherein the at least one monomer A is selected from quaternized dimethylaminoethyl acrylate, quaternized dimethylaminoethyl methacrylate, diallyldimethylammonium chloride, propyltrimethyl ammonium acrylamide chloride, propyltrimethylmethacrylamide ammonium chloride and mixtures thereof, and that the dialdehyde is selected from the group consisting of glyoxal, glutaraldehyde, furane-dialdehyde, adipaldehyde, succinaldehyde, dialdehyde starch, 2,2 dimethoxyethanal, diepoxy compounds, and mixtures thereof.

13. The water-soluble dialdehyde-functionalized polymer according to claim 2 , wherein the at least one non-ionic monomer B is selected from acrylamide, acrylonitrile, methacrylamide and in that the dialdehyde is glyoxal.

14. The water-soluble dialdehyde-functionalized polymer according to claim 12 , wherein it comprises between 500 and 50,000 ppm of compound I, based on to the total weight of monomers A and B;

and wherein it comprises between 500 and 50,000 ppm of compound II, based on to the total weight of monomers A and B.

15. The water-soluble dialdehyde-functionalized polymer according to claim 14 , wherein compound II is selected from: N,N-dimethylacrylamide, N,N-diethylacrylamide, N,N-isopropylacrylamide, N-methylolacrylamide and mixtures thereof.

16. A method for sequentially preparing a water-soluble dialdehyde-functionalized polymer, comprising the following steps:

a) formation of a solution (S1) comprising at least a first fraction (F1) containing (1) at least one monomer selected from monomers A and B and (2) at least one compound selected from compounds I and II;

the at least one monomer A being a cationic monomer or an anionic monomer;

the at least one monomer B being a non-ionic monomer;

the at least one compound I being selected from: allylsulfonic acid, methallysulfonic acid, allyl disulfonic acid, methallyl disulfonic acid, salts and mixtures thereof;

the at least one compound II being of formula (1), different from at least monomer B:

R 1 and R 2 being, independently of one another, a hydrogen atom or a methyl group, an ethyl group, an isopropyl group or a CH 2 —OH group;

R 1 and R 2 not both being a hydrogen atom;

b) polymerization 1 (PO1) of the fraction F1 to form a solution of a first gradient polymer (PG1);

c) addition, to the solution comprising PG1, of a second fraction (F2) containing (1) at least one monomer selected from monomers A and B and (2) at least one compound selected from compounds I and II;

d) polymerization 2 (PO2) of fraction F2 on PG1 in order to form a solution of a second gradient polymer (PG2);

e) addition, to the solution comprising PG2, of a third fraction (F3) containing (1) at least one monomer selected from monomers A and B and (2) at least one compound selected from compounds I and II;

f) polymerization 3 (PO3) of fraction F3 on PG2, in order to form a solution comprising a base polymer;

g) dilution of the solution comprising the base polymer and reaction between at least one dialdehyde and the base polymer in order to obtain a water-soluble dialdehyde polymer;

at least one of the fractions F1, F2 or F3 contains at least one monomer A,

at least one of the fractions F1, F2 or F3 contains at least one monomer B,

at least one of the fractions F1, F2 or F3 contains at least one compound I and

at least one of the fractions F1, F2 or F3 contains at least one compound II,

with monomer A being distinct from a mixture of cationic monomer and anionic monomer,

when monomer A is anionic, the water-soluble dialdehyde-functionalized polymer does not comprise any cationic monomer,

when monomer A is cationic, the water-soluble dialdehyde-functionalized polymer does not comprise any anionic monomer, with the exception of compound I.

17. The method according to claim 16 , wherein at least one of fractions F1, F2 or F3 is different from the others.

18. The method according to claim 16 , wherein an initiator is added continuously throughout the polymerization process, and in that the dialdehyde is glyoxal.

19. The method according to claim 16 , wherein, after step f) of polymerization (PO3), the method comprises an aging step of between 10 and 100 minutes.

20. The method according to claim 16 , wherein the dialdehyde reaction comprises at least the following steps:

g1) dilution of the solution comprising the base polymer, in order to form a diluted solution of the base polymer (SD1);

g2) optionally adjustment of the pH of SD1 to at least 10;

g3) addition of at least one dialdehyde into the solution obtained in step g1) or g2), in order to form a diluted solution (SD2);

g4) optionally acidification to a pH comprised between 2 and 4 of the solution obtained in step g3), in order to form a diluted solution (SD3).

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2024
From: FAUCHER, GATIEN; FOUGEROUSE, DAMIEN; BARRIERE, CYRIL
To: SNF GROUP
Reel/Frame 069621/0726 →
Priority Claims (1)
FR 2206322 · Jun 24, 2022 · national
Continuity (1)
Related Publication 20250171568A1 · May 29, 2025
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