Polymer suitable as a thickener

Patent metadata

Field	Value
Publication number	US-11370912-B2
Application number	US-201816604733-A
Country	US
Kind code	B2
Filing date	Apr 12, 2018
Priority date	Apr 13, 2017
Publication date	Jun 28, 2022
Grant date	Jun 28, 2022

Abstract

The invention relates to polymer comprising structural units according to formula (I), R1—X—(C═O)—NH—R2—NH—(C═O)—O—POA-R3—(O—POA-R4)n wherein R1 represents an organic group terminated by a hydrocarbyl group having 6 to 50 carbon atoms, X represents O or N—R5, wherein R5 represents a hydrogen atom or a hydrocarbyl group having 1 to 30 carbon atoms, R2 represents a hydrocarbyl group comprising an aromatic group and having 6 to 40 carbon atoms, POA represents a polyoxyalkylene group, R3 represents an organic group having 2 to 40 carbon atoms, n is an integer from 1 to 6, R4 is independently selected from —(C═O)—NH—R2—NH—(C═O)—NH—R1, —R6, wherein R6 represents a hydrogen atom or an aliphatic or aromatic group having 1 to 24 carbon atoms, and wherein the polymer has an average of at least 1.8 end groups R1 per molecule, a number average molecular weight in the range of 2000 to 100000 Daltons, and a polydispersity in the range of 1.0 to 5.0, wherein the quotient of the polydispersity divided by (n+1) is less than 1.0.

First claim

The invention claimed is:

1. A polymer comprising structural units according to formula (I),
R 1 —X—(C═O)—NH—R 2 —NH—(C═O)—O—POA-R 3 —(O—POA-R 4 ) n

wherein
R 1 represents an organic group terminated by a hydrocarbyl group having 6 to 50 carbon atoms,
X represents O or N—R 5 , wherein R 5 represents a hydrogen atom or a hydrocarbyl group having 1 to 30 carbon atoms,
R 2 represents a hydrocarbyl group comprising an aromatic group and having 6 to 40 carbon atoms,
POA represents a polyoxyalkylene group,
R 3 represents an organic group having 2 to 40 carbon atoms,
n is an integer from 1 to 6,
R 4 is independently selected from
—(C═O)—NH—R 2 —NH—(C═O)—X—R 1 ,
—(C═O)—NH—R 1 ,
—R 6 , wherein R 6 represents a hydrogen atom or an aliphatic or aromatic group having 1 to 24 carbon atoms,
and wherein the polymer has an average of at least 1.8 end groups R 1 per molecule, a number average molecular weight in the range of 2000 to 100000 g/mol (Daltons), and a polydispersity in the range of 1.0 to 5.0, wherein a quotient of the polydispersity divided by (n+1) is less than 1.0.

2. The polymer according to claim 1 , wherein X is 0.

3. The polymer according to claim 1 , wherein at least one R 1 represents a polyoxyalkylene group terminated by a hydrocarbyl group having 6 to 50 carbon atoms.

4. The polymer according to claim 1 , wherein at least one R 1 represents a hydrocarbyl group having 6 to 30 carbon atoms.

5. The polymer according to claim 1 , wherein the polyoxyalkylene group comprises repeating units selected from —[C 2 H 4 —O]— and —[C 3 H 6 —O]—.

6. The polymer according to claim 1 , having a content of the structural units according to formula (I) of at least 70% by weight, calculated on the total mass of the polymer.

7. A process for preparing a polymer according to claim 1 , comprising reacting a compound of formula
R 1 —X—(C═O)—NH—R 2 —NCO  (II)

and a compound of formula
HO—POA-R 3 —(O—POA-R 4 ) n   (III),

wherein
R 1 represents an organic group terminated by a hydrocarbyl group having 6 to 50 carbon atoms,
X represents O or N—R 5 , wherein R 5 represents a hydrogen atom or a hydrocarbyl group having 1 to 30 carbon atoms,
R 2 represents a hydrocarbyl group comprising an aromatic group and having 6 to 40 carbon atoms,
POA represents a polyoxyalkylene group,
R 3 represents an organic group having 2 to 40 carbon atoms,
n is an integer from 1 to 6, and
R 4 is independently selected from
—(C═O)—NH—R 2 —NH—(C═O)—X—R 1 ,
—(C═O)—NH—R 1 ,
—R 6 , wherein R 6 represents a hydrogen atom or an aliphatic or aromatic group having 1 to 24 carbon atoms.

8. The process according to claim 7 , wherein the compound of formula (II) is obtained by reacting a diisocyanate of formula OCN—R 2 —NCO (IV) and a compound of formula R 1 —XH (V).

9. The process according to claim 8 , wherein the isocyanate groups of the diisocyanate of formula (IV) differ in reactivity towards the compound of formula (V).

10. A composition comprising
a) a continuous aqueous liquid phase,
b) the polymer according to claim 1 dissolved in the continuous aqueous liquid phase, and
c) a hydrophobic component dispersed in the continuous aqueous liquid phase.

11. The composition according to claim 10 , wherein the hydrophobic component is an organic film-forming binder.

12. The composition according to claim 10 , further comprising solid particles.

13. The composition according to claim 12 , wherein the solid particles are selected from pigments, fillers, and combinations thereof.

14. An additive composition comprising
a) 10.0 to 60.0% by weight of the polymer according to claim 1 ,
b) 40.0 to 90.0% by weight of water,
c) 0.0 to 1.0% by weight of a biocide, and
d) 0.0 to 75.0% by weight of a viscosity depressant.

Assignees

• Byk Chemie Gmbh

Inventors

• Bernert Dominika
• Nagelsdiek René
• Steinmetz Alan L
• Adams Justin
• Zody George M
• Huff Wesley A
• Leutfeld Daniela

Classifications

• C08G18/2825

  having at least 6 carbon atoms · CPC title

• C08G18/7806

  containing -N-C=0 groups · CPC title

• C08L75/08 Primary

  from polyethers · CPC title

• C08G18/4825

  Polyethers containing two hydroxy groups (C08G18/4833 - C08G18/5096 take precedence) · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title