IP Library Granted Patent US 12,275,883
Granted Patent B2
US 12,275,883 · App. 17/427,946 · Granted Apr 15, 2025

Multifunctional additive compounds

Inventor: Haibo Zhao (The Woodlands, TX)
C09K15/22A61K8/86A61Q19/00C08G65/3328C08G65/33303C10L1/238C10L1/2387C10L10/04C10M149/14C10L2200/0423C10L2230/085C10M2201/02C10M2217/04C10M2217/041C10M2217/06C10N2030/12C10N2030/24
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Quick Facts
Patent No.
US 12,275,883
App. No.
17/427,946
Granted
Apr 15, 2025
Kind
B2
Abstract

The present disclosure generally relates to a multifunctional additive obtained from the reaction of: (a) an intermediate obtained from the reaction of maleic anhydride and a polyoxyalkylene monoamine; and (b) an amine compound comprising a primary amine group and/or a secondary amine group and its use in a variety of applications, including, but not limited to: as a corrosion inhibitor or friction modifier in aqueous and non-aqueous systems; in fuel deposit control agents; as a dispersant in pigment, asphalt and cement compositions; and as a detergent.

Claims (16)

1. An additive compound obtained by the reaction of: (a) an intermediate formed from the reaction of maleic anhydride and a polyoxyalkylene monoamine; and (b) an amine compound comprising a primary amine group and/or a secondary amine group having the formula (I):

wherein R 5 , R 7 and R 8 , which can be the same or different, in each case are a hydrogen atom or a hydrocarbon group having 1 carbon atom to 60 carbon atoms, Y is —O—, p is an integer equal to or higher than 1 and m is an integer between 1 to 10, and each R 6 is independently a hydrogen atom or a hydrocarbon group having 1 carbon atom to 4 carbon atoms.

2. The additive compound of claim 1 , wherein p is an integer between 1 and 10, R 5 , R 7 and R 8 are hydrogen and R 6 is hydrogen or methyl.

3. The additive compound of claim 1 , wherein the polyoxyalkylene monoamine is a compound having a formula:

where R 1 is hydrogen, a C 1 to C 20 alkyl group or a C 6 aryl group optionally substituted with one or more C 1 to C 10 alkyl groups; w, x, and y are each independently an integer between zero to about 100, subject to the proviso that w+x+y is greater than two; d is 0 or 1; and, R b is a C 1 to C 10 alkyl group.

4. A method of forming an additive compound comprising reacting (a) an intermediate formed from the reaction of maleic anhydride and a polyoxyalkylene monoamine with (b) an amine compound comprising a primary amine group and/or a secondary amine group having the formula (I):

wherein R 5 , R 7 and R 8 , which can be the same or different, in each case are a hydrogen atom or a hydrocarbon group having 1 carbon atom to 60 carbon atoms, Y is —O—, p is an integer equal to or higher than 1 and m is an integer between 1 and 10, and each R 6 is independently a hydrogen atom or a hydrocarbon group having 1 carbon atom to 4 carbon atoms.

5. The method of claim 4 , wherein an amount of the amine compound (b) used in the reaction with the intermediate (a) is within a molar ratio of the amine compound (b) to maleic anhydride used in forming the intermediate (a) of about 1.5:1 to about 1:1.5.

6. A composition comprising the additive compound of claim 1 and at least one of a solvent, a surfactant or an auxiliary.

7. The composition of claim 6 , wherein the additive compound is present in an amount of from 0.0001% by weight to less than 50% by weight, based on the total weight of the composition.

8. A performance chemical formulation comprising the composition of claim 6 , wherein the additive compound is present in the performance chemical formulation in an amount ranging from about 0.001% by weight to about 40% by weight, based on the total weight of the performance chemical formulation.

9. A personal care formulation comprising the composition of claim 6 , wherein the additive compound is present in the performance chemical formulation in an amount ranging from about 0.001% by weight to about 40% by weight, based on the total weight of the personal care formulation.

10. A corrosion inhibiting composition comprising the additive of claim 1 and an aqueous fluid.

11. The corrosion inhibiting composition of claim 10 , wherein the aqueous fluid is selected from freshwater, brackish water, sea water, waste water, a mixture of water and salts, a mixture of water and alcohol, a mixture of water and acid, a mixture of water and caustic and a combination thereof.

12. A corrosion inhibiting composition comprising the additive of claim 1 and a non-aqueous fluid.

13. The corrosion inhibiting composition of claim 12 , wherein the non-aqueous fluid is a hydrocarbon fuel.

Assignments (3)
SECURITY INTEREST Recorded May 4, 2026
From: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN NANOCOMP LLC; HUNTSMAN PETROCHEMICAL LLC
To: CITIBANK N.A.
Reel/Frame 075498/0663 →
PATENT SECURITY AGREEMENT Recorded Mar 10, 2026
From: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN NANOCAMP LLC; HUNTSMAN PETROCHEMICAL LLC
To: CITIBANK, N.A.
Reel/Frame 075106/0238 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2021
From: ZHAO, HAIBO
To: HUNTSMAN PETROCHEMICAL LLC
Reel/Frame 057061/0380 →