Surfactants and methods of making and using same

Patent metadata

Field	Value
Publication number	US-9454082-B2
Application number	US-201414763841-A
Country	US
Kind code	B2
Filing date	Jan 9, 2014
Priority date	Jan 29, 2013
Publication date	Sep 27, 2016
Grant date	Sep 27, 2016

Abstract

Anionic surfactants have a formula: R f SO 2 N(H)—CH 2 CH(CH 3 )OH; or R f SO 2 N(H)—CH 2 CH 2 O) x H, where x is an integer from 2-6. Rf is a fluoroalkyl group having 3 to 8 carbon atoms. Neutral surfactants having a formula: (a) R f —SO 2 N[CH 2 CH(CH 3 )OH] 2 ; (b) R f SO 2 N[CH 2 CH(CH 3 )OH][(CH 2 CH 2 O) n H], where n is an integer from 1-6; (c) R f SO 2 N(R)[(CH 2 CH 2 O) p H], where p is an integer from 2-6, and R is an alkyl group having 1 to 4 carbon atoms; or (d) R f SO 2 N[(CH 2 CH 2 O) q H][(CH 2 CH 2 O) m H], where q is an integer from 1-6 and m is an integer from 3-6. R f is a fluoroalkyl group having 3 to 8 carbon atoms.

First claim

The invention claimed is:

1. A fluorinated sulfonamide surfactant composition comprising:
a neutral surfactant according to the formula:
R f SO 2 N[CH 2 CH(CH 3 )OH] 2 ;
R f SO 2 N[CH 2 CH(CH 3 )OH][(CH 2 CH 2 O) n H], where n is an integer from 1-6; or

R f SO 2 N[(CH 2 CH 2 O) q H][(CH 2 CH 2 O) m H], where q is an integer from 1-6, m is an integer from 1-6, and (q+m)≧3; and
a solvent comprising water and one or more alcohols;
wherein R f is a fluoroalkyl group having 3 to 8 carbon atoms.

2. A fluorinated sulfonamide surfactant composition comprising:
an anionic surfactant according to the formula:
R f SO 2 N(H)—CH 2 CH(CH 3 )OH;
R f SO 2 N(H)—(CH 2 CH 2 O) x H, where x is an integer from 2-6; or
R f SO 2 N(H)—CH 2 CH 2 OH; and

a neutral surfactant according to the formula:
R f SO 2 N[CH 2 CH(CH 3 )OH] 2 ;
R f SO 2 N[CH 2 CH(CH 3 )OH][(CH 2 CH 2 O) n H], where n is an integer from 1-6;
R f SO 2 N[(CH 2 CH 2 O) q H][(CH 2 CH 2 O) m H], where q is an integer from 1-6, m is an integer from 1-6, and q+m≧3; or
R f SO 2 N[CH 2 CH 2 OH] 2 ; and

a solvent;
wherein R f is a fluoroalkyl group having 3 to 8 carbon atoms;
with the proviso that if the composition comprises appreciable amounts of only one anionic surfactant and only one neutral surfactant, and the anionic surfactant is R f SO 2 N(H)—CH 2 CH 2 OH, then the neutral surfactant is not R f SO 2 N[CH 2 CH 2 OH] 2 .

3. A composition according to claim 2 , wherein x is an integer from 2-3.

4. A composition according to claim 3 , wherein n is an integer from 1-3, p is an integer from 2-3, and q is an integer from 1-3.

5. A composition according to claim 4 , wherein m is an integer ≦3.

6. A composition according to claim 2 , wherein m is 3.

7. A composition according to claim 2 , wherein the fluoroalkyl group is saturated.

8. A composition according to claim 2 , wherein the fluoroalkyl group is straight chain.

9. A composition according to claim 2 , wherein the fluoroalkyl group is a perfluoroalkyl group.

10. A composition according to claim 2 , wherein the fluoroalkyl group has 4 to 6 carbon atoms.

11. A composition according to claim 2 , wherein the fluoroalkyl group is a saturated perfluoroalkyl group having 4 to 6 carbon atoms.

12. A composition according to claim 2 , wherein the fluoroalkyl group is a saturated perfluoroalkyl group having 4 carbon atoms.

13. A composition according to claim 2 , wherein either the anionic or neutral surfactant includes at least one oligomeric ethylene oxide group bonded to the sulfonamide nitrogen atom, wherein the oligomeric ethylene oxide group has 2-6 ethylene oxide repeat units.

14. A composition according to claim 2 , wherein if the composition comprises a solvent, the solvent comprises water, an organic liquid, or combinations thereof.

15. A composition according to claim 2 , wherein either the anionic or neutral surfactant includes two oligomeric ethylene oxide group bonded to the sulfonamide nitrogen atom, wherein the oligomeric ethylene oxide group has 2-6 ethylene oxide repeat units.

16. A method of treating a surface of a photoresist material, the method comprising:
exposing the photoresist material to a composition according to claim 2 .

Assignees

• 3M Innovative Properties Co

Inventors

• Lamanna William M
• Savu Patricia M
• Kehren Jason M

Classifications

• G03F7/42

  Stripping or agents therefor · CPC title

• C08F290/065

  Polyamides; Polyesteramides; Polyimides · CPC title

• G03F7/40 Primary

  Treatment after imagewise removal, e.g. baking · CPC title

• C07C311/00

  Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups · CPC title

• C08F290/062

  Polyethers · CPC title