Method for the hydrolysis of a polymer

Patent metadata

Field	Value
Publication number	US-12018113-B2
Application number	US-201917276247-A
Country	US
Kind code	B2
Filing date	Sep 13, 2019
Priority date	Sep 14, 2018
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

Methods for producing final polymer A are provided that comprise the following steps:
(A) providing a starting polymer V, the starting polymer V being obtainable by radical polymerization of the monomers (i), (ii), (iii), and (iv) as described herein in the amounts provided herein; and (B) hydrolyzing the provided starting polymer V under alkaline conditions to obtain the final polymer A, wherein the N—C(═O)R 1 groups of formula (I) at least partially hydrolyze the monomers (i) polymerized into the starting polymer V to form primary amino groups.

Certain final polymers A obtained are useful for a method for producing paper or cardboard comprising adding certain final polymers A to a first aqueous pulp suspension, dewatering the obtained second aqueous pulp suspension containing certain final polymers A on a water-permeable substrate to a wet paper structure, and further dewatering of the wet paper structure into a paper or cardboard.

First claim

The invention claimed is:

1. A method for producing final polymer A comprising the following steps:
(A) providing a starting polymer V, wherein the starting polymer V is obtained by
radical polymerization of the monomers
(i) 58 to 90 mol % of a monomer of the formula I

in which R 1 denotes H or C 1 -C 6 alkyl,

(ii) 3 to 39 mol % of a C 1 -C 4 alkyl ester of acrylic acid or of a C 1 -C 4 alkyl ester of methacrylic acid,
(iii) 1 to 25 mol % of a monoethylenically unsaturated carboxylic acid, a monoethylenically unsaturated sulfonic acid or a monoethylenically unsaturated phosphonic acid, or salt forms thereof,
(iv) 0 to 35 mol % of one or more ethylenically unsaturated monomers which are different from a monomer (i), (ii) and (iii),
wherein the total amount of all monomers (i), (ii), (iii) and (iv) is 100 mol %, and

(B) hydrolyzing the provided starting polymer V under alkaline conditions to obtain the final polymer A,
wherein the N—C(═O)R 1 groups of the formula (I) of the monomers (i) polymerized into the starting polymer V at least partially hydrolyze to form primary amino groups, and wherein a viscosity peak during hydrolyzing of the provided starting polymer V is low to none.

2. The method according to claim 1 , wherein in step (B), the ester groups of the monomers (ii) polymerized into the starting polymer V at least partially react and at least part of the reaction is the formation of five-membered lactam structural units with the obtained primary amino groups or the formation of carboxylic acid groups or salt forms thereof.

3. The method according to claim 1 , wherein for the radical polymerization
(i) 58 to 89 mol % of a monomer of the formula I,
(ii) 5 to 39 mol % of a C 1 -C 4 alkyl ester of acrylic acid or of a C 1 -C 4 alkyl ester of methacrylic acid,
(iii) 1 to 25 mol % of a monoethylenically unsaturated carboxylic acid, a monoethylenically unsaturated sulfonic acid or a monoethylenically unsaturated phosphonic acid, or salt forms thereof,
(iv) 0 to 25 mol % of one or more ethylenically unsaturated monomers which are different from a monomer (i), (ii) and (iii),
are used.

4. The method according to claim 1 , wherein for the radical polymerizing
(i) 58 to 83 mol % of a monomer of the formula I,
(ii) 8 to 39 mol % of a C 1 -C 4 alkyl ester of acrylic acid or of a C 1 -C 4 alkyl ester of methacrylic acid,
(iii) 2 to 25 mol % of a monoethylenically unsaturated carboxylic acid, a monoethylenically unsaturated sulfonic acid or a monoethylenically unsaturated phosphonic acid, or salt forms thereof,
(iv) 0 to 25 mol % of one or more ethylenically unsaturated monomers which are different from a monomer (i), (ii) and (iii),
are used.

5. The method according to claim 1 , wherein the monomer (iii) is used in an amount of 3 to 25 mol %.

6. The method according to claim 1 , wherein in step (B), at least 50 to 100% of the monomers (i) polymerized into the starting polymer V are hydrolyzed, based on the number of all monomers (i) polymerized into the starting polymer V.

7. The method according to claim 2 , wherein in step (B), at least 50 to 100% of the monomers (ii) polymerized into the starting polymer V are reacted, based on the number of all monomers (ii) polymerized into the starting polymer V.

8. The method according to claim 1 , wherein in step (B), at least 70 and at most 99.5% of the polymerized monomers (i) are hydrolyzed, based on the number of all monomers (i) polymerized into the starting polymer V.

9. The method according to claim 1 , wherein the monomer (i) is N-vinylformamide with R 1 =H in formula I.

10. The method according to claim 1 , wherein the monomer (ii) is a C 1 -C 3 alkyl ester of acrylic acid or C 1 alkyl ester of methacrylic acid.

11. The method according to claim 10 , wherein the monomer (ii) is a C 1 -C 2 alkyl ester of acrylic acid.

12. The method according to claim 1 , wherein the monomer (ii) is ethyl acrylate.

13. The method according to claim 1 , wherein the monomer (iii) is a monoethylenically unsaturated carboxylic acid or a monoethylenically unsaturated sulfonic acid, or salt forms thereof.

14. The method according to claim 1 , wherein the monomer (iii) is acrylic acid, methacrylic acid, vinylsulfonic acid or 2-acrylamido-2-methylpropanesulfonic acid, or salt forms thereof.

15. The method according to claim 1 , wherein for the radical polymerization, the monomers
(i) 60 to 83 mol % of N-vinylformamide,
(ii) 8 to 21 mol % ethyl acrylate,
(iii) 2 to 21 mol % of acrylic acid or methacrylic acid or salt forms thereof,
(iv) 0 to 24 mol % of one or more ethylenically unsaturated monomers which are different from a monomer (i), (ii) and (iii),
are used.

16. The method according to claim 1 , wherein the monomers (iv) comprise an amount of 0 to 6 mol % of acrylamide, the molar percent being based on the total number of all monomers (i), (ii), (iii) and (iv) and the total number of all monomers being 100 mol %.

17. The method according to claim 1 , wherein in step (B), the ester groups of the monomers (ii) polymerized into the starting polymer V are at least partially reacted and at least part of the reaction is the formation of five-membered lactam structural units with the obtained primary amino groups.

18. The method according to claim 1 , wherein in step (B), a base is used in a numerical amount corresponding to between 30 and 150 mol % of the number of monomers (i) polymerized into starting polymer V.

19. A method of producing paper or cardboard comprising the following steps:
(AC) adding a final polymer A to a first aqueous pulp suspension whereby a second aqueous pulp suspension comprising final polymer A is created,
wherein the final polymer A is obtained by
radical polymerization of the monomers
(i) 58 to 90 mol % of a monomer of the formula I

in which R 1 denotes H or C 1 -C 6 alkyl,

(ii) 3 to 39 mol % of a C 1 -C 4 alkyl ester of acrylic acid or of a C 1 -C 4 alkyl ester of methacrylic acid,
(iii) 1 to 25 mol % of a monoethylenically unsaturated carboxylic acid, a monoethylenically unsaturated sulfonic acid or a monoethylenically unsaturated phosphonic acid, or salt forms thereof,
(iv) 0 to 35 mol % of one or more ethylenically unsaturated monomers which are different from a monomer (i), (ii), (iii) and (iv),
wherein acrylonitrile or methacrylonitrile are used in an amount of 0 to 9 mol %, wherein the total amount of all monomers (i), (ii), (iii) and (iv) is 100 mol % to obtain a starting polymer V, and
hydrolyzing the provided starting polymer V under alkaline conditions to obtain the final polymer A,
wherein the N—C(═O)R 1 groups of the formula (I) of the monomers (i) polymerized into the starting polymer V at least partially hydrolyze to form primary amino groups,
wherein the ester groups of the monomers (ii) polymerized into the starting polymer V are at least partially reacted and at least part of the reaction is the formation of five-membered lactam structural units with the obtained primary amino groups or the formation of carboxylic acid groups or salt forms thereof, and wherein a viscosity peak during hydrolyzi

Assignees

• Solenis Tech Lp

Inventors

• Haehnle Hans-Joachim
• Esser Anton
• Isermann Ralph

Classifications

• D21H17/45

  Nitrogen-containing groups · CPC title

• C08F226/02 Primary

  by a single or double bond to nitrogen · CPC title

• C08F220/06

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title

• C08F220/585

  and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS] · CPC title

• C08F220/1802

  C2-(meth)acrylate, e.g. ethyl (meth)acrylate · CPC title