IP Library › Granted Patent US 12,071,578
Granted Patent B2
US 12,071,578 · App. 17/373,713 · Granted Aug 27, 2024

Branched amino acid surfactants for electronics products

Inventor: Edward Asirvatham (Chatham, NJ)
Assignee: AdvanSix Resins & Chemicals LLC
C09K13/00G03F7/325H01L21/30604
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Quick Facts
Patent No.
US 12,071,578
App. No.
17/373,713
Granted
Aug 27, 2024
Kind
B2
Abstract

Pre-texturing agents, etchants, and photoresist stripping agents 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 (72)

1. A formulation for a pre-texturing agent, 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, and iodide; and

one or more solvents.

2. The formulation of claim 1 , further comprising one or more acids.

3. The formulation of claim 1 , further comprising one or more bases.

4. The formulation of claim 1 , further comprising one or more chelating agents.

5. 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-(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:

6. A formulation for a pre-texturing agent, comprising:

at least one surfactant of 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, and iodide; and

one or more defoaming agents.

7. The formulation of claim 6 , further comprising one or more acids.

8. The formulation of claim 6 , further comprising one or more bases.

9. The formulation of claim 6 , further comprising one or more chelating agents.

10. The formulation of claim 6 , further comprising one or more solvents.

11. The formulation of claim 6 , 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-(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:

12. A formulation for an etchant, comprising:

at least one surfactant of 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, and iodide; and

hydrofluoric acid (HF).

13. The formulation of claim 12 , further comprising one or more oxidizing agents.

14. The formulation of claim 12 , further comprising one or more complexing agents.

15. The formulation of claim 12 , wherein the surfactant is surfactant comprises at least one of:

6-((2-butyloctyl)oxy)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, 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:

16. A formulation for a photoresist stripping formulation, comprising:

at least one surfactant of 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, and iodide; and

an alkanolamine.

17. The formulation of claim 16 , further comprising a sulfoxide.

18. The formulation of claim 16 , further comprising a sulfone.

19. The formulation of claim 16 , further comprising a glycol ether.

20. The formulation of claim 16 , 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-(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:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 6, 2021
From: ASIRVATHAM, EDWARD
To: ADVANSIX RESINS & CHEMICALS LLC
Reel/Frame 057103/0923 →
Continuity (2)
Provisional Application 63051187 · Jul 13, 2020
Related Publication 20220017821A1 · Jan 20, 2022