IP Library Granted Patent US 8,013,179
Granted Patent B2
US 8,013,179 · App. 12/454,742 · Granted Sep 6, 2011

Anionic acid-labile surfactants and methods of use

Assignee: Protea Biosciences, Inc.
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Quick Facts
Patent No.
US 8,013,179
App. No.
12/454,742
Granted
Sep 6, 2011
Kind
B2
Abstract

Anionic acid-labile surfactants may generally comprise compounds represented by the formulas: and wherein R 1 is independently selected from —(CH 2 ) 0-9 CH 3 , R 2 is selected from the group consisting of —H and —(CH 2 ) 0-5 CH 3 , Y is an anion, X is a cation, and n is an integer from 1 to 8. Methods of making and using the anionic acid-labile surfactants are also disclosed.

Claims (22)

1. A compound of the formula:

wherein R 1 is independently selected from —(CH 2 ) 0-9 CH 3 , R 2 is selected from the group consisting of —H and —(CH 2 ) 0-5 CH 3 , Y is selected from the group consisting of —SO 3 − and —PO 3 − , X is a cation selected from the group consisting of sodium, potassium, lithium, and ammonium ions, and n is an integer from 1 to 8.

2. A compound of the formula:

wherein each R 1 is —(CH 2 ) 5 CH 3 , R 2 is —CH 3 , Y is —SO 3 − , X is sodium, and n is 1.

3. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 5 CH 3 , R 2 is —CH 3 , and n is 1.

4. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 6 CH 3 , R 2 is —CH 3 , and n is 1.

5. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 5 CH 3 , R 2 is —CH 3 , and n is 2.

6. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 6 CH 3 , R 2 is —CH 3 , Y is —SO 3 − , X is sodium, and n is 1.

7. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 5 CH 3 , R 2 is —CH 3 , Y is —SO 3 − , X is sodium, and n is 2.

8. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 6 CH 3 , R 2 is —CH 3 , Y is —SO 3 − , X is sodium, and n is 2.

9. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 5 CH 3 , R 2 is —CH 3 , Y is —SO 3 − , X is potassium, and n is 1.

10. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 5 CH 3 , R 2 is —CH 3 , Y is —SO 3 − , X is potassium, and n is 2.

11. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 6 CH 3 , R 2 is —CH 3 , Y is —SO 3 − , X is potassium, and n is 1.

12. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 6 CH 3 , R 2 is —CH 3 , Y is —SO 3 − , X is potassium, and n is 2.

13. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 5 CH 3 , R 2 is —CH 3 , Y is —PO 3 − , X is sodium, and n is 1.

14. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 5 CH 3 , R 2 is —CH 3 , Y is —PO 3 − , X is sodium, and n is 2.

15. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 6 CH 3 , R 2 is —CH 3 , Y is —PO 3 − , X is sodium, and n is 1.

16. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 6 CH 3 , R 2 is —CH 3 , Y is —PO 3 − , X is sodium, and n is 2.

17. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 5 CH 3 , R 2 is —CH 3 , Y is —PO 3 − , X is potassium, and n is 1.

18. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 5 CH 3 , R 2 is —CH 3 , Y is —PO 3 − , X is potassium, and n is 2.

19. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 6 CH 3 , R 2 is —CH 3 , Y is —PO 3 − , X is potassium, and n is 1.

20. The compound of claim 1 , wherein each R 1 is —(CH 2 ) 6 CH 3 , R 2 is —CH 3 , Y is —PO 3 − , X is potassium, and n is 2.

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 6, 2018
From: SUMMIT RESOURCES, INC.
To: NEW RIVER HOLDINGS, LLC
Reel/Frame 045460/0077 →
COURT ORDER Recorded Apr 6, 2018
From: PROTEA BIOSCIENCES, INC.; PROTEA BIOSCIENCES GROUP, INC.
To: SUMMIT RESOURCES, INC.
Reel/Frame 045459/0974 →
BILL OF SALE Recorded Apr 6, 2018
From: NEW RIVER HOLDINGS, LLC
To: NEW RIVER LABS, LLC
Reel/Frame 045852/0820 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2018
From: PROTEA BIOSCIENCES, INC.
To: SUMMIT RESOURCES, INC.
Reel/Frame 044821/0192 →
SECURITY INTEREST Recorded Jan 4, 2018
From: PROTEA BIOSCIENCES GROUP, INC.
To: SUMMIT RESOURCES, INC.
Reel/Frame 044532/0975 →
SECURITY INTEREST Recorded Sep 6, 2017
From: PROTEA BIOSCIENCES GROUP INC.
To: SUMMIT RESOURCES INC.
Reel/Frame 043496/0858 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2010
From: POWELL, MATTHEW JACOB; RAZUNGUZWA, TRUST TARIRO; O'DOHERTY, GEORGE AUGUSTINE; LI, MIAOSHENG
To: PROTEA BIOSCIENCES, INC.
Reel/Frame 023871/0713 →
Continuity (2)
Provisional Application 61055746 · May 23, 2008
Related Publication 20090292136A1 · Nov 26, 2009