IP Library Granted Patent US 9,012,390
Granted Patent B2
US 9,012,390 · App. 12/310,048 · Granted Apr 21, 2015

Fluorocarbon emulsion stabilizing surfactants

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Quick Facts
Patent No.
US 9,012,390
App. No.
12/310,048
Granted
Apr 21, 2015
Kind
B2
Abstract

Surfactants (e.g., fluorosurfactants) for stabilizing aqueous or hydrocarbon droplets in a fluorophilic continuous phase are presented. In some embodiments, fluorosurfactants include a fluorophilic tail soluble in a fluorophilic (e.g., fluorocarbon) continuous phase, and a headgroup soluble in either an aqueous phase or a lipophilic (e.g., hydrocarbon) phase. The combination of a fluorophilic tail and a headgroup may be chosen so as to create a surfactant with a suitable geometry for forming stabilized reverse emulsion droplets having a disperse aqueous or lipophilic phase in a continuous, fluorophilic phase. In some embodiments, the headgroup is preferably non-ionic and can prevent or limit the adsorption of molecules at the interface between the surfactant and the discontinuous phase. This configuration can allow the droplet to serve, for example, as a reaction site for certain chemical and/or biological reactions. In another embodiment, aqueous droplets are stabilized in a fluorocarbon phase at least in part by the electrostatic attraction of two oppositely charged or polar components, one of which is at least partially soluble in the dispersed phase, the other at least partially soluble in the continuous phase. One component may provide collodial stability of the emulsion, and the other may prevent the adsorption of biomolecules at the interface between a component and the discontinous phase. Advantageously, surfactants and surfactant combinations of the invention may provide sufficient stabilization against coalescence of droplets, without interfering with processes that can be carried out inside the droplets.

Claims (20)

1. An emulsion, comprising:

an aqueous dispersed phase;

a continuous phase comprising a fluorinated oil; and

a surfactant comprising a block copolymer that includes a perfluorinated polyether (PFPE)block coupled to a polyethylene glycol (PEG) block via an amide bond, wherein the surfactant comprises a formula —(C n F 2n O) x —(C m F 2m ) y —CONH— and n, m, x, and y are positive integers.

2. An emulsion of claim 1 , wherein the dispersed phase has an average diameter greater than or equal to about 50 nm and less than or equal to about 200 microns.

3. An emulsion of claim 1 , wherein the dispersed phase has an average diameter of no more than about 200 microns.

4. A method comprising performing a chemical and/or biological reaction in the dispersed phase of claim 1 .

5. The emulsion of claim 1 , wherein the dispersed phase has an average diameter greater than or equal to about 50 nm.

6. The emulsion of claim 1 , wherein the dispersed phase comprises an aqueous solution comprising a biological molecule.

7. The emulsion of claim 6 , wherein the biological molecule comprises a nucleic acid.

8. The emulsion of claim 7 , wherein the biological molecule comprises an oligonucleotide.

9. The emulsion of claim 1 , wherein the dispersed phase does not coalesce for at least 30 minutes at 25° C. and 1 atm.

10. The emulsion of claim 1 , wherein the surfactant has a molecular weight of greater than 1000 g/mol.

11. The emulsion of claim 1 , wherein x is greater than or equal to 8.

12. The emulsion of claim 11 wherein x is greater than 10.

13. The emulsion of claim 1 , wherein the PFPE comprises a formula —(CF(CF 3 )CF 2 O) x —, and wherein x is greater than or equal to 8.

14. The emulsion of claim 13 , wherein x is greater than 10.

15. The emulsion of claim 1 , wherein the PFPE comprises a formula —(CF(CF 3 )CF 2 O) x —CF(CF 3 )CONH—, and wherein x is greater than or equal to 8.

16. The emulsion of claim 15 , wherein x is greater than 10.

17. The emulsion of claim 1 , wherein the dispersed phase comprises buffers, salts, nutrients, therapeutic agents, drugs, hormones, antibodies, analgesics, anticoagulants, anti-inflammatory compounds, antimicrobial compositions, cytokines, growth factors, interferons, lipids, oligonucleotides polymers, polysaccharides, polypeptides, protease inhibitors, cells, nucleic acids, RNA, DNA, vasoconstrictors or vasodilators, vitamins, minerals, or stabilizers.

Assignments (8)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 7, 2019
From: RAINDANCE TECHNOLOGIES, INC.
To: BIO-RAD LABORATORIES, INC.
Reel/Frame 049109/0498 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 2, 2018
From: MEDICAL RESEARCH COUNCIL
To: UNITED KINGDOM RESEARCH AND INNOVATION
Reel/Frame 046469/0108 →
RELEASE OF SECURITY INTEREST Recorded Feb 17, 2017
From: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II (CAYMAN) L.P.; PARALLEL INVESTMENT OPPORTUNITIES PARTNERS II L.P.; CRG ISSUER 2015-1
To: RAINDANCE TECHNOLOGIES, INC.
Reel/Frame 041290/0585 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2014
From: AGRESTI, JEREMY
To: PRESIDENT AND FELLOWS OF HARVARD COLLEGE
Reel/Frame 032729/0311 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2014
From: AHN, KEUNHO; GUERRA, RODRIGO; HOLTZE, CHRISTIAN; WEITZ, DAVID
To: PRESIDENT AND FELLOWS OF HARVARD COLLEGE
Reel/Frame 032674/0229 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 4, 2014
From: HUTCHISON, JOHN BRIAN
To: RAINDANCE TECHNOLOGIES, INC.
Reel/Frame 032137/0898 →
SHORT-FORM PATENT SECURITY AGREEMENT Recorded Sep 17, 2013
From: RAINDANCE TECHNOLOGIES, INC.
To: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "A" L.P.; PARALLEL INVESTMENT OPPORTUNITIES PARTNERS II L.P.
Reel/Frame 031267/0376 →
CONFIRMATORY LICENSE Recorded Dec 30, 2009
From: HARVARD UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 023715/0920 →