IP Library › Granted Patent US 11,787,967
Granted Patent B2
US 11,787,967 · App. 17/373,706 · Granted Oct 17, 2023

Branched amino acid surfactants for inks, paints, and adhesives

Inventor: Edward Asirvatham (Chatham, NJ)
Assignee: AdvanSix Resins & Chemicals LLC
C09D11/54C09D9/04C09J11/06
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Quick Facts
Patent No.
US 11,787,967
App. No.
17/373,706
Granted
Oct 17, 2023
Kind
B2
Abstract

Inks, paints, adhesives, and paint strippers may be formulated to include one or more branched surfactants, from one or more surfactant classes, such as derivatives of amino acids that have surface-active properties.

Claims (142)

1. A formulation for an ink fixer fluid, comprising:

at least one surfactant of the following formula:

wherein R 1 and R 2 are independently chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

n is an integer from 2 to 5 (including 2 and 5);

R 3 is C 5 -C 12 alkyl;

R 4 is C 3 -C 10 alkyl;

the terminal nitrogen is optionally further substituted with R 5 , wherein R 5 is chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

an optional counterion may be associated with the compound and, if present, the counterion may be selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate;

one or more solvents;

a fixer agent; and

water.

2. The formulation of claim 1 , wherein the fixer agent is a metal carboxylate.

3. The formulation of claim 1 , further comprising at least one of:

a humectant;

an acid;

an aqueous vehicle; and

a colorant.

4. The formulation of claim 1 , wherein the surfactant comprises at least one of:

6-((2-butyloctyl)oxy)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

6-((2-butyloctyl)oxy)-N,N-dimethyl-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

6-(dodecyloxy)-N,N-dimethyl-6-oxohexan-1-aminium chloride, having the following formula:

4-((6-((2-butyloctyl)oxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

2-butyloctyl 6-(dimethylamino)hexanoate N-oxide, having the following formula:

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium chloride, having the following formula:

and

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

5. A formulation for a paint, comprising:

at least at least one surfactant of the following formula:

wherein R 1 and R 2 are independently chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

n is an integer from 2 to 5 (including 2 and 5);

R 3 is C 5 -C 12 alkyl;

R 4 is C 3 -C 10 alkyl;

the terminal nitrogen is optionally further substituted with R 5 , wherein R 5 is chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

an optional counterion may be associated with the compound and, if present, the counterion may be selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate;

a latex; and

water.

6. The formulation of claim 5 , further comprising at least one of:

one or more driers;

one or more solvents; and

one or more pigments.

7. The formulation of claim 5 , wherein the surfactant comprises at least one of:

6-((2-butyloctyl)oxy)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

6-((2-butyloctyl)oxy)-N,N-dimethyl-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

6-(dodecyloxy)-N,N-dimethyl-6-oxohexan-1-aminium chloride, having the following formula:

4-((6-((2-butyloctyl)oxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

2-butyloctyl 6-(dimethylamino)hexanoate N-oxide, having the following formula:

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium chloride, having the following formula:

and

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

8. A formulation for a paint, comprising:

at least one surfactant of the following formula:

wherein R 1 and R 2 are independently chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

n is an integer from 2 to 5 (including 2 and 5);

R 3 is C 5 -C 12 alkyl;

R 4 is C 3 -C 10 alkyl;

the terminal nitrogen is optionally further substituted with R 5 , wherein R 5 is chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

an optional counterion may be associated with the compound and, if present, the counterion may be selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate;

a binder; and

water.

9. The formulation of claim 8 , further comprising at least one of:

one or more driers;

one or more solvents; and

one or more pigments.

10. The formulation of claim 8 , wherein the surfactant comprises at least one of:

6-((2-butyloctyl)oxy)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

6-((2-butyloctyl)oxy)-N,N-dimethyl-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

6-(dodecyloxy)-N,N-dimethyl-6-oxohexan-1-aminium chloride, having the following formula:

4-((6-((2-butyloctyl)oxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

2-butyloctyl 6-(dimethylamino)hexanoate N-oxide, having the following formula:

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium chloride, having the following formula:

and

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

11. A formulation for an adhesive, comprising:

at least one surfactant of the following formula:

wherein R 1 and R 2 are independently chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

n is an integer from 2 to 5 (including 2 and 5);

R 3 is C 5 -C 12 alkyl;

R 4 is C 3 -C 10 alkyl;

the terminal nitrogen is optionally further substituted with R 5 , wherein R 5 is chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

an optional counterion may be associated with the compound and, if present, the counterion may be selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate;

an adhesive; and

water.

12. The formulation of claim 11 , further comprising a filling agent.

13. The formulation of claim 11 , wherein the surfactant comprises at least one of:

6-((2-butyloctyl)oxy)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

6-((2-butyloctyl)oxy)-N,N-dimethyl-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

6-(dodecyloxy)-N,N-dimethyl-6-oxohexan-1-aminium chloride, having the following formula:

4-((6-((2-butyloctyl)oxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

2-butyloctyl 6-(dimethylamino)hexanoate N-oxide, having the following formula:

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium chloride, having the following formula:

and

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

14. A formulation for a paint stripper, comprising:

at least one surfactant of the following formula:

wherein R 1 and R 2 are independently chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

n is an integer from 2 to 5 (including 2 and 5);

R 3 is C 5 -C 12 alkyl;

R 4 is C 3 -C 10 alkyl;

the terminal nitrogen is optionally further substituted with R 5 , wherein R 5 is chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

an optional counterion may be associated with the compound and, if present, the counterion may be selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate;

1,2-dichloroethylene; and

water.

15. The formulation of claim 14 , further comprising at least one of:

a wax;

a corrosion inhibitor;

an organic solvent; and

a thickener.

16. The formulation of claim 14 , wherein the surfactant comprises at least one of:

6-((2-butyloctyl)oxy)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

6-((2-butyloctyl)oxy)-N,N-dimethyl-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

6-(dodecyloxy)-N,N-dimethyl-6-oxohexan-1-aminium chloride, having the following formula:

4-((6-((2-butyloctyl)oxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

2-butyloctyl 6-(dimethylamino)hexanoate N-oxide, having the following formula:

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium chloride, having the following formula:

and

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

17. A formulation for a paint stripper, comprising:

at least one surfactant of the following formula:

wherein R 1 and R 2 are independently chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

n is an integer from 2 to 5 (including 2 and 5);

R 3 is C 5 -C 12 alkyl;

R 4 is C 3 -C 10 alkyl;

the terminal nitrogen is optionally further substituted with R 5 , wherein R 5 is chosen from hydrogen, an oxygen atom, and C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl may be substituted with carboxylates, hydroxyls, sulfonyls, or sulfonates;

an optional counterion may be associated with the compound and, if present, the counterion may be selected from the group consisting of chloride, bromide, iodide, and 4-methylbenzenesulfonate;

1,2-dichloroethylene;

one or more co-solvents; and

water.

18. The formulation of claim 17 , wherein the one or more co-solvents are selected from aromatic alcohols, aromatic ethers, and aliphatic alcohols.

19. The formulation of claim 17 , further comprising at least one of:

a wax;

a corrosion inhibitor;

an organic solvent; and

a thickener.

20. The formulation of claim 17 , wherein the surfactant comprises at least one of:

6-((2-butyloctyl)oxy)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

6-((2-butyloctyl)oxy)-N,N-dimethyl-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

6-(dodecyloxy)-N,N-dimethyl-6-oxohexan-1-aminium chloride, having the following formula:

4-((6-((2-butyloctyl)oxy)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

2-butyloctyl 6-(dimethylamino)hexanoate N-oxide, having the following formula:

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium chloride, having the following formula:

and

6-((2-butyloctyl)oxy)-6-oxohexan-1-aminium 4-methylbenzenesulfonate, having the following formula:

Assignments (2)
SECURITY INTEREST Recorded Aug 14, 2026
From: ADVANSIX INC.; ADVANSIX RESINS & CHEMICALS LLC
To: CITIZENS BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 076163/0178 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 6, 2021
From: ASIRVATHAM, EDWARD
To: ADVANSIX RESINS & CHEMICALS LLC
Reel/Frame 057104/0037 →
Continuity (2)
Provisional Application 63051191 · Jul 13, 2020
Related Publication 20220010161A1 · Jan 13, 2022