IP Library › Granted Patent US 11,999,890
Granted Patent B2
US 11,999,890 · App. 17/871,208 · Granted Jun 4, 2024

Surfactants for electronics

Inventor: Edward Asirvatham (Chatham, NJ)
Assignee: AdvanSix Resins and Chemicals LLC
C09K13/06C07F7/0838C09K13/00
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Quick Facts
Patent No.
US 11,999,890
App. No.
17/871,208
Granted
Jun 4, 2024
Kind
B2
Abstract

Pre-texturing agents, etchants, and photoresist stripping agents may be formulated to include one or more surfactants, from one or more surfactant classes, such as siloxane derivatives of amino acids that have surface-active properties.

Claims (31)

1. A formulation for an etchant, comprising:

at least one surfactant of Formula I,

wherein R 1 and R 2 may be the same or different, and comprise at least one group selected from the group consisting of C 1 -C 6 alkyl, optionally the C 1 -C 6 alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;

n is an integer from 1 to 12;

the terminal nitrogen is optionally further substituted with R 3 , wherein R 3 is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C 1 -C 6 alkyl;

an optional counterion associated with the compound which, if present, is selected from the group consisting of chloride, bromide, and iodide; and

hydrofluoric acid (HF).

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

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

4. The formulation of claim 1 , wherein n is 5 .

5. The formulation of claim 1 , wherein the surfactant is 6 -(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexanamide, having the following formula:

6. The formulation of claim 1 , wherein the surfactant is 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexaminium chloride, having the following formula:

7. The formulation of claim 1 , wherein the surfactant is 3 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

8. The formulation of claim 1 , wherein the surfactant is 6 -((3-(1,1, 1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexan-1-amine oxide, having the following formula:

9. The formulation of claim 1 , wherein the surfactant is 4-((6-((3-(1,1, 1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

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

at least one surfactant of Formula I,

wherein R 1 and R 2 may be the same or different, and comprise at least one group selected from the group consisting of C 1 -C 6 alkyl, optionally the C 1 -C 6 alkyl may include one or more of oxygen, nitrogen, or sulfur atoms or groups that include at least one of these atoms, and the alkyl chain may be optionally substituted with one or more substituents selected from the group consisting of hydroxyl, amino, amido, sulfonyl, sulfonate, carbonyl, carboxyl, and carboxylate;

n is an integer from 1 to 12;

the terminal nitrogen is optionally further substituted with R 3 , wherein R 3 is selected from the group consisting of hydrogen, oxygen, hydroxyl, and C 1 -C 6 alkyl;

an optional counterion associated with the compound which, if present, is selected from the group consisting of chloride, bromide, and iodide; and

an alkanolamine.

11. The formulation of claim 10 , further comprising a sulfoxide.

12. The formulation of claim 10 , further comprising a sulfone.

13. The formulation of claim 10 , further comprising a glycol ether.

14. The formulation of claim 10 , wherein n is 5 .

15. The formulation of claim 10 , wherein the surfactant is 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexanamide, having the following formula:

16. The formulation of claim 10 , wherein the surfactant is 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexaminium chloride, having the following formula:

17. The formulation of claim 10 , wherein the surfactant is 3 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide, having the following formula:

18. The formulation of claim 10 , wherein the surfactant is 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexan-1-amine oxide, having the following formula:

19. The formulation of claim 10 , wherein the surfactant is 4-((6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane-1-sulfonate, having the following formula:

Assignments (1)
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 →
Continuity (3)
Division 17127048 · Dec 18, 2020
Provisional Application 62970356 · Feb 5, 2020
Related Publication 20220380669A1 · Dec 1, 2022
Cited By (2)
US 12,459,963 US 12,466,846