Heat-stabilising agent

Patent metadata

Field	Value
Publication number	US-12528904-B2
Application number	US-202017785386-A
Country	US
Kind code	B2
Filing date	Dec 2, 2020
Priority date	Dec 16, 2019
Publication date	Jan 20, 2026
Grant date	Jan 20, 2026

Abstract

Polyurethane heat-stabilizing agents may help resist temperature changes and preparations of an aqueous composition which may be resistant to temperature changes due to the use of such an agent (P). The viscosity may be thermally stabilized by such an aqueous composition in a wide temperature range and for many shear gradient values.

First claim

The invention claimed is:

1 . A heat-stabilizing agent (P), comprising:
a polyurethane (P1) comprising, in polymerized form: a diisocyanate compound (A1), a polyisocyanate compound (A2), or combination thereof in a range of from 0.1 to 28 wt. %; a polyhydroxylated compound (B) in a range of from 2 to 99.5 wt. %; and a monoisocyanate compound (C1) of formula I, a monohydroxylated compound (C2) of formula II, a compound (C3) of formula III, or a combination thereof, in a range of from 0.4 to 70 wt. %,
T 1 -NCO (I), T 2 -OH (II), R 1 -(OE) a -(OP) b -R 2   (III)

wherein T 1 and T 2 are independently a straight C 30 -C 36 -alkyl group or a branched C 30 -C 36 -alkyl group, a and b are independently 0 or an integer or decimal less than 150, a or b being different from 0, EO is independently a CH 2 CH 2 O group, PO is independently a combination of (i) at least one CH 2 CH 2 O group with (ii) at least one group chosen CH(CH 3 )CH 2 O and/or CH 2 CH(CH 3 )O, R 1 is a group comprising at least one labile hydrogen atom, and R 2 is independently a straight C 30 -C 36 -alkyl group or a branched C 30 -C 36 -alkyl group, or a polyurethane (P2) prepared in the absence of any diisocyanate compound, comprising, in reacted form: a polyisocyanate compound (A2) in a range of from 0.1 to 28 wt. %; a polyhydroxylated compound (B) in a range of from 2 to 99.5 wt. %; and a monoisocyanate compound (C1) of formula I, a monohydroxylated compound (C2) of formula II, a compound (C3) of formula III, or a combination thereof, in a range of from 0.4 to 70 wt. %; and wherein the agent (P), when added to an aqueous solution at from 0.1 to 2 wt. %, relative to total composition weight, creates an aqueous composition, the aqueous composition having, for a temperature variation in a range of from 5 to 50° C., a decrease in viscosity measured for a shear gradient in a range from 0.1 to 100 s −1 , of less than 70% relative to an initial viscosity value of the aqueous composition.

2 . The agent (P) of claim 1 , wherein the polyisocyanate compound (A2) is present and comprises more than 2 isocyanate groups.

3 . The agent (P) of claim 1 , wherein the polyhydroxylated compound (B) is:
a compound (B1) of formula IV:
(HO)-L n -(OH)   (IV)

L being independently a poly (alkyleneglycol) residue, and n being independently a number in a range of from 30 to 1,000; a compound (B1) of formula (IV) combined with a non-alkoxylated compound (B2) comprising at least three hydroxyl groups; a polyalkoxylated compound (B3) comprising at least three hydroxyl groups; a compound (B4) of formula (V):
HO-(OA) p -N(Q)-(OA) q -OH   (V),

Q independently being a straight C 28 -C 40 -alkyl group or a branched C 28 -C 40 -alkyl group, OA independently being an ethoxylated group or a combination of ethoxylated (—CH 2 CH 2 O—) groups and propoxylated (—CH 2 C(CH 3 )O—) groups, and p and q independently being a number in a range of from 50 to 200; or a combination thereof.

4 . The agent (P) of claim 1 , for which the compound (B) is:
a compound (B1) of formula (IV):
(HO)-L n -(OH)   (IV)

L independently being a poly(ethylene glycol) residue, and n independently being a number in a range of from 50 to 400; a compound (B2) comprising three hydroxyl groups; a polyethoxylated compound (B3) comprising three hydroxyl groups; a compound (B4) of formula (V) wherein Q is independently a branched C 30 -C 36 -alkyl group or a straight C 30 -C 36 -alkyl group.

5 . The agent (P) of claim 1 , wherein the compounds (B) has a molar mass (Mw) measured by SEC in a range of from 1,500 to 40,000 g/mol.

6 . The agent (P) of claim 1 , wherein the monoisocyanate compound (C1) is a compound of formula (I) wherein T 1 is independently a straight C 30 -C 36 -akyl group or a branched C 30 -C 36 -alkyl group, or
wherein the monoisocyanate compound (C1) is prepared by a separate reaction of (i) at least one compound comprising at least one labile hydrogen atom and of (ii) at least one diisocyanate compound, or wherein the monohydroxylated compound (C2) is a compound of formula (II) wherein T 2 is represents a straight C 30 -C 36 -alkyl group or a branched C 30 -C 36 -alkyl group, or wherein the compound (C3) is a compound of formula (III) wherein a is an integer or decimal ranging from 5 to 100 , b is 0, R 1 is a group comprising at least one labile hydrogen atom and R 2 is a straight C 30 -C 36 -alkyl group or a branched C 30 -C 36 -alkyl group.

7 . The agent (P) of claim 1 , prepared by at least one polymerization reaction of:
the monomer (A) in a range of from 0.2 to 26 wt. %. the monomer (B) in a range of from 6 to 99.3 wt. %, and the monomer (C) in a range of from 0.5 to 68 wt. %, relative to total monomer weight.

8 . A method for preparing an aqueous composition that is heat-resistant to temperature changes, the method comprising:
adding the heat-stabilizing agent (P) of claim 1 , to the aqueous composition.

9 . The method of claim 8 wherein the aqueous composition comprises the heat-stabilizing agent (P) in a range of from 0.05 to 5 wt. %, relative to total composition weight.

10 . The method of claim 8 , wherein the aqueous composition has, for a temperature variation in a range of from 5 to 50° C., a viscosity measured for a shear gradient in a range from:
1 to 1,000 s −1 , in a range of from 30 to 98% of an initial viscosity value of the aqueous composition, or
1 to 100 s −1 , in a range of from 30 to 98% of the initial viscosity value of the aqueous composition, or
1 to 100 s −1 , in a range of from 30 to 98% of the initial viscosity value of the aqueous composition, or
0.1 to 1 s −1 , in a range of from 40 to 98% of the initial viscosity value of the aqueous composition.

11 . An aqueous composition, made by the method of claim 8 .

12 . The composition of claim 11 , which is a hydraulic binder composition, a bonding agent composition, a detergent composition, a cosmetic composition, an ink composition, an aqueous paper coating composition, or a coating composition.

13 . A method for heat stabilizing a viscosity of an aqueous composition, the method comprising:
adding the heat-stabilizing agent (P) of claim 1 to the aqueous composition, wherein, for a temperature ranging from 5° C. to 50° C., a decrease in viscosity measured for a shear gradient ranging from: 0.1 to 1,000 s −1 is less than 70% relative to an initial viscosity of the aqueous composition, or 0.1 to 100 s −1 is less than 70% relative to the initial viscosity of the aqueous composition, or 1 to 100 s −1 is less than 70% relative to the initial viscosity of the aqueous composition, or 0.1 to 1 s − is less than 60% relative to the initial viscosity of the aqueous composition.

14 . The method of claim 13 , wherein the heat-stabilizing agent (P) is added to the aqueous composition in an amount in a range of from 0.05 to 5 wt. %, relative to total composition weight.

15 . A method for improving resistance to temperature changes of an aqueous composition, the method comprising:
adding the heat-stabilizing agent (P) of claim 1 to the aqueous composition.

16 . The heat-stabilizing agent (P) of claim 1 , comprising:
a polyurethane (P1) comprising, in polymerized form: isophorone diisocyanate (IPDI) in a range of from 0.1 to 28 wt. %; polyethylene glycol with a molecular mass (Mw) of 8,000 g/mol at from 2 to 99.5 wt. %; and a C32-alkyl ethoxylated alcohol with 25 equivalents of ethylene oxide in a range of from 0.4 to 70 wt. %.

17 . A heat-stabilizing agent (P), c

Assignees

• Coatex Sas

Inventors

• Magny Benoit
• Matter Yves
• Ruhlmann Denis
• Suau Jean Marc

Classifications

• C08G18/3221

  hydroxylated esters of carboxylic acids other than higher fatty acids · CPC title

• C08G18/283

  Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds · CPC title

• C08G18/227

  of antimony, bismuth or arsenic · CPC title

• C08G18/755 Primary

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

• C08G18/4833 Primary

  Polyethers containing oxyethylene units · CPC title