IP Library Granted Patent US 12662573
Granted Patent B2
US 12662573 · App. 18/020,226 · Granted Jun 23, 2026

Hydrophobically-modified associative thickener polymers process for the preparation and uses thereof

Inventors: Kelly Anne Brush (Newark, DE); Venkataram Krishnan (Avondale, PA); Zeena Kottukapally Cherian (Exton, PA); Todd A. Brugel (Wilmington, DE)
Assignee: HERCULES LLC
C08G65/338C08G65/2603C08L71/00C09D5/00C09D7/43C09D7/61C09D7/65C09D171/02C09K8/68C08G2150/00C08G2650/08C08G2650/54C09K8/508
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Quick Facts
Patent No.
US 12662573
App. No.
18/020,226
Granted
Jun 23, 2026
Kind
B2
Abstract

Disclosed is a hydrophobically-modified associative thickener polymer prepared from a reaction mixture comprising a) a polytetrahydrofuran having a formula (I): b) at least one active hydrogen-containing compound; c) a gem-polyhalide with an alkali hydroxide; or d) a polyglycidyl ether with an alkali hydroxide; e) optionally, a hydrophobe-containing compound, wherein m is an integer in a range from 2 to 750; also disclosed are the aqueous protective coating compositions; further disclosed is a process to prepare a hydrophobically-modified associative thickener polymer.

Claims (29)

1 . A hydrophobically-modified associative thickener polymer prepared from a reaction mixture comprising:

a) a polytetrahydrofuran having a formula (I):

b) at least one active hydrogen-containing compound;

c) a gem-polyhalide with an alkali hydroxide; or

d) a polyglycidyl ether with an alkali hydroxide; and

e) a monofunctional hydrophobe-containing component,

wherein m is an integer in a range from 2 to 750,

wherein the active hydrogen containing compound(s) are present in an amount from about 50 wt % to about 99 wt %.

2 . A hydrophobically-modified associative thickener polymer of claim 1 , wherein the monofunctional hydrophobe-containing component with an epoxide functionality is represented by the formula (VI):

wherein AA is a substituted or unsubstituted compound having a functionality selected from the group consisting of alkyl, alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, arylalkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, and polycyclic moieties, optionally containing at least one heteroatom.

3 . A hydrophobically-modified associative thickener polymer of claim 2 , wherein the monofunctional hydrophobe-containing component with an epoxide functionality is selected from the group consisting of allylglycidyl ether (AGE), 2-ethylhexylglycidyl ether (EHGE), hexadecylglycidyl ether (HAGE-13), oxirane [(docosyloxy), methyl] (HAGE-22), naphthylglycidyl ether (NGE), n-butylglycidyl ether (n-BGE), iso-butylglycidyl ether (iso-BGE), E10P glycidyl ether, glycidyl ether based on cashew nutshell liquid, and glycidyl ester.

4 . A hydrophobically-modified associative thickener polymer of claim 1 , wherein the polyglycidyl ether is represented by formula (VIII):

wherein A is a substituted or unsubstituted compound having a functionality selected from the group consisting of alkyl, alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, arylalkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, and polycyclic moieties, optionally containing at least one heteroatom; and s is an integer in the range from 2 to 4.

5 . A hydrophobically-modified associative thickener polymer of claim 4 , wherein the polyglycidyl ether is represented by formula (IX):

wherein R 1 is H or methyl; and t is an integer in the range from 1 to 500.

6 . A process to prepare a hydrophobically-modified associative thickener polymer of claim 1 , comprising:

i) a reactor is charged with polytetrahydrofuran, at least one active hydrogen-containing compound, and an alkali hydroxide while heating the contents of the reactor to at least 70° C.;

ii) the contents of the reactor are mixed under vacuum of around 29 inches Hg,

iii) a gem-polyhalide is added to the reaction mixture of step ii) and the contents of the reactor are mixed;

iv) optionally, the temperature of the reaction mixture is increased;

v) a monofunctional hydrophobe-containing component is added, and the contents of the reactor are further mixed; and

vi) the contents of the reactor are discharged and allowed to cool to 20-25° C. to obtain a solid polymer.

7 . A process to prepare a hydrophobically-modified associative thickener polymer of claim 1 , comprising:

i) a reactor is charged with polytetrahydrofuran, at least one active hydrogen-containing compound, and an alkali hydroxide while heating the contents of the reactor to at least 70° C.;

ii) the contents of the reactor are mixed under vacuum of around 29 inches Hg,

iii) a polyglycidyl ether is added to the reaction mixture of step ii) and the contents of the reactor are mixed;

iv) optionally, the temperature of the reaction mixture is increased;

v) a monofunctional hydrophobe-containing component is added, and the contents of the reactor are further mixed; and

vi) the contents of the reactor are discharged and allowed to cool to 20-25° C. to obtain a solid polymer.