Hydrophobically modified alkylene oxide polymer mixture

Patent metadata

Field	Value
Publication number	US-12331193-B2
Application number	US-202017765083-A
Country	US
Kind code	B2
Filing date	Oct 29, 2020
Priority date	Nov 13, 2019
Publication date	Jun 17, 2025
Grant date	Jun 17, 2025

Abstract

The present invention relates to a composition comprising a mixture of a first and a second hydrophobically modified alkylene oxide polymer, wherein the first hydrophobically modified alkylene oxide polymer is endcapped with at least one first hydrophobic group functionalized with a secondary amine or a salt thereof, or a tertiary amine or a salt thereof;
and wherein the second hydrophobically modified alkylene oxide polymer is endcapped with at least one second hydrophobic group, structure I:

where R 1 , R 2 , m, and n are as defined herein. The present invention also relates to a method for preparing the composition. The composition of the present invention provides an associative thickener with an excellent balance of as-is viscosity and temperature stability over a wide temperature range.

First claim

The invention claimed is:

1. A composition comprising a mixture of a first and a second hydrophobically modified alkylene oxide polymer, wherein the first hydrophobically modified alkylene oxide polymer is endcapped with at least one first hydrophobic group functionalized with a secondary amine or a salt thereof, or a tertiary amine or a salt thereof; and wherein the second hydrophobically modified alkylene oxide polymer is endcapped with at least one second hydrophobic group, structure I:

wherein the dotted line represents the point of attachment of the hydrophobic group of structure I to the alkylene oxide polymer backbone; where R 1 is from C 1 -C 10 -alkyl; R 2 is from C 1 -C 6 -alkyl; m is from 5 to 40; and n is from 0 to 50, with the proviso that when m is from 5 to 9, n is from 0 to 10, wherein the first and second hydrophobically modified alkylene oxide polymers are hydrophobically modified ethylene oxide urethane polymers, and wherein the mole: mole ratio of first hydrophobic groups to second hydrophobic groups is in the range of from 15:85 to 75:25.

2. The composition of claim 1 wherein R 1 is C 1 -C 8 alkyl; R 2 is methyl or ethyl; m is from 10 to 30; and n is from 0 to 20.

3. The composition of claim 2 wherein R 1 is C 2 -C 6 alkyl; R 2 is methyl; m is from 12 to 20; and n is 0.

4. The composition of claim 2 wherein the at least one first hydrophobic group has a calculated Log P in the range of from 2 to 12.

5. The composition of claim 3 wherein the at least one first hydrophobic group is a remnant of a compound selected from the group consisting of 2-(t-butylamino) ethanol; 2-(dibutylamino) ethanol; 2-(dioctylamino) ethanol; 2-(diheptylamino) ethanol; 2-(bis (2-ethylhexyl) amino) ethanol; 2-(dihexylamino) ethanol; 3-(dibutylamino) propanol; 2-(dibutylamino) ethylamine; 3-(dibutylamino) propylamine; N-benzyl-N-methylethanolamine; 1-(dibutylamine)-2-butanol; 4-amino-1-benzyl-piperidine; 1-(benzyl (2-hydroxyethyl) amino)-3-butoxypropan-2-ol; 1-(benzyl (2-hydroxyethyl) amino)-3-(2-ethylhexyl) oxypropan-2-ol; 1-[bis (phenylmethyl) amino]-3- [(2-butyl) oxyl]-2-propanol; 1-[bis (phenylmethyl) amino]-3-[(2-ethylhexyl) oxyl]-2-propanol; and a dibenzylaminopolyalkylene oxide of the type:

where R 3 is methyl or ethyl and p is from 1 to 10.

6. The composition of claim 1 wherein the first hydrophobically modified ethylene oxide urethane polymer is endcapped with two first hydrophobic groups; and the second hydrophobically modified ethylene oxide urethane polymer is endcapped with two second hydrophobic groups of structure I, wherein the composition further comprises a hydrophobically modified ethylene oxide urethane polymer endcapped with both first and second hydrophobic groups.

7. The composition of claim 6 wherein the mole: mole ratio of the hydrophobically modified ethylene oxide urethane polymer capped with a first hydrophobic group and a second hydrophobic group to the hydrophobically modified ethylene oxide urethane polymers capped with first hydrophobic groups only and second hydrophobic groups only is in the range of from 1:3 to 1:1, which composition is in the form of an aqueous solution; wherein the first hydrophobic group has a has a calculated log P in the range of from 4 to 10.

8. The composition of claim 7 wherein the mole: mole ratio of first hydrophobic groups to second hydrophobic groups is in the range of from 25:75 to 50:50.

9. The composition of any of claim 1 which further comprises pigment, binder, and at least one other component selected from the group consisting of surfactants, coalescents, defoamers, opaque polymers, and extenders.

10. A method of preparing a hydrophobically modified ethylene oxide urethane polymer blend comprising the step of contacting under reactive conditions, a) a water-soluble polyethylene glycol; b) a stoichiometric excess of a diisocyanate relative to the polyethylene glycol; a c1) a first hydrophobic compound functionalized with a secondary or a tertiary amine or a quaternary ammonium salt; and c2) a second hydrophobic compound of structure Ia, to form the hydrophobically modified ethylene oxide urethane polymer, wherein the hydrophobic compound of structure Ia is as follows:

where R 1 is from C 1 -C 10 -alkyl; R 2 is from C 1 -C 6 -alkyl; m is from 5 to 40; and n is from 0 to 50, with the proviso that when m is from 5 to 9, n is from 0 to 10, and wherein the mole:mole ratio of first hydrophobic compound to second hydrophobic compound is in the range of from 15:85 to 75:25.

11. A composition comprising a hydrophobically modified alkylene oxide polymer co-endcapped with first and second hydrophobic groups, wherein the first hydrophobic group is functionalized with a secondary amine or a salt thereof, or a tertiary amine or a salt thereof; and the second hydrophobic group is represented by structure I:

wherein the dotted line represents the point of attachment of the hydrophobic group of structure I to the alkylene oxide polymer backbone; where R 1 is from C 1 -C 10 -alkyl; R 2 is from C 1 -C 6 -alkyl; m is from 5 to 40; and n is from 0 to 50, with the proviso that when m is from 5 to 9, n is from 0 to 10, wherein the hydrophobically modified alkylene oxide polymer is a hydrophobically modified ethylene oxide urethane polymer, and wherein the mole:mole ratio of first hydrophobic groups to second hydrophobic groups is in the range of from 15:85 to 75:25.

12. The composition of claim 11 wherein R 1 is C 1 -C 8 alkyl; R 2 is methyl or ethyl; m is from 10 to 30; and n is from 0 to 20.

13. The composition of claim 12 wherein R 1 is C 2 -C 6 alkyl; R 2 is methyl; m is from 12 to 20; and n is 0.

14. The composition of claim 12 wherein the at least one first hydrophobic group has a calculated Log P in the range of from 2 to 12.

15. The composition of claim 13 wherein the at least one first hydrophobic group is a remnant of a compound selected from the group consisting of 2-(t-butylamino) ethanol; 2-(dibutylamino) ethanol; 2-(dioctylamino) ethanol; 2-(diheptylamino) ethanol; 2-(bis (2-ethylhexyl) amino) ethanol; 2 -(dihexylamino) ethanol; 3-(dibutylamino) propanol; 2-(dibutylamino) ethylamine; 3-(dibutylamino) propylamine; N-benzyl-N-methylethanolamine; 1-(dibutylamine)-2-butanol; 4-amino-1-benzyl -piperidine; 1-(benzyl (2-hydroxyethyl) amino)-3-butoxypropan-2-ol; 1-(benzyl (2-hydroxyethyl) amino)-3-(2-ethylhexyl) oxypropan-2-ol; 1-[bis (phenylmethyl) amino]-3-[(2-butyl) oxyl]-2-propanol; 1-[bis (phenylmethyl) amino]-3-[(2-ethylhexyl) oxyl]-2-propanol; and a dibenzylaminopolyalkylene oxide of the type:

where R 3 is methyl or ethyl and p is from 1 to 10.

16. The composition of claim 13 which further comprises a second hydrophobically modified alkylene oxide polymer endcapped with two first hydrophobic groups and a third hydrophobically modified alkylene oxide polymer endcapped with two second hydrophobic groups, where the second and third hydrophobically modified alkylene oxide polymers are hydrophobically modified ethylene oxide urethane polymers; and where the total mole:mole ratio of first hydrophobic g

Assignees

• Rohm & Haas

Inventors

• Rabasco John J
• Saucy Daniel A

Classifications

• C09D5/04

  Thixotropic paints · CPC title

• C08G65/33348

  containing isocyanate group · CPC title

• C08G65/3312

  acyclic · CPC title

• C08G65/2609

  containing aliphatic hydroxyl groups · CPC title

• C08G18/758 Primary

  containing two or more cycloaliphatic rings · CPC title