IP Library Granted Patent US 9,498,761
Granted Patent B2
US 9,498,761 · App. 14/687,388 · Granted Nov 22, 2016

Fluorocarbon emulsion stabilizing surfactants

Inventors: Christian Holtze (Medford, MA); David A. Weitz (Cambridge, MA); John Brian Hutchison (Medford, MA)
Assignees: Raindance Technologies, Inc.; President and Fellows of Harvard College
B01F17/005B01F17/0035C08G65/007C08G65/332C08G65/337C08G81/00C08L71/00C08G2650/48C08L2201/52C08L2205/05
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,498,761
App. No.
14/687,388
Granted
Nov 22, 2016
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 colloidal stability of the emulsion, and the other may prevent the adsorption of biomolecules at the interface between a component and the discontinuous 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 (30)

1. A surfactant, comprising a block copolymer including a perfluorinated polyether (PFPE) block coupled to a polyethylene glycol (PEG) block via an amide bond, wherein the PFPE block comprises a formula of F(CF(CF 3 )CF 2 O) x —CF(CF 3 )CONH—, wherein x is an integer greater than or equal to 8; and the PEG block comprises a formula of—(C n H 2n O) y —or —(C n H 2n O) y —CH 3 , wherein n is a positive integer and y is an integer greater than or equal to 10.

2. The surfactant of claim 1 , wherein the surfactant comprises one block of PFPE and one block of PEG.

3. The surfactant of claim 1 , wherein the surfactant comprises two blocks of PFPE and one block of PEG.

4. A composition comprising the surfactant of claim 1 .

5. The composition of claim 4 , further comprising a hydrophobic liquid.

6. The composition of claim 4 , further comprising an aqueous liquid.

7. The composition of claim 4 , further comprising a fluorinated oil and an aqueous liquid.

8. The composition of claim 7 , wherein the aqueous liquid additionally comprises biological molecules.

9. The composition of claim 8 , wherein the biological molecules comprise nucleic acids.

10. A method of forming aqueous droplets, comprising:

providing a microfluidic device;

providing an aqueous liquid to the microfluidic device;

providing a fluorinated liquid to the microfluidic device;

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

forming aqueous droplets in the fluorinated liquid in the presence of the surfactant.

11. The method of claim 10 , wherein the microfluidic device comprises a first channel intersecting a second channel at a junction.

12. The method of claim 11 , wherein the aqueous liquid flows in the first channel and the fluorinated liquid flows in the second channel.

13. The method of claim 12 , wherein the aqueous droplets are formed at the junction.

14. The method of claim 13 , wherein the microfluidic device includes a nozzle, and the droplets form after the aqueous and fluorinated liquids pass through the nozzle.

15. The method of claim 10 , wherein the aqueous droplets comprise biological molecules.

16. The method of claim 15 , wherein the biological molecules comprise nucleic acids.

17. The method of claim 10 , wherein the aqueous droplets comprise buffers, salts, nutrients, therapeutic agents, drugs, hormones, antibodies, analgesics, anticoagulants, anti-inflammatory compounds, antimicrobial compositions, cytokines, growth factors, interferons, lipids, polymers, polysaccharides, polypeptides, protease inhibitors, cells, RNA, DNA, vasoconstrictors, vasodilators, vitamins, minerals, or stabilizers.

18. The method of claim 10 , wherein the aqueous droplets comprise fluorescent molecules.

19. The method of claim 10 , wherein the surfactant comprises the formula —(CF(CF 3 )CF 2 O) x —CF(CF 3 )CONH—, wherein x is greater than or equal to 8.

20. A method of forming aqueous droplets, comprising:

providing a microfluidic device;

providing an aqueous liquid to the microfluidic device;

providing a fluorinated liquid to the microfluidic device;

providing a surfactant of claim 1 , and

forming aqueous droplets in the fluorinated liquid in the presence of the surfactant.

Assignments (3)
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 Sep 8, 2016
From: HOLTZE, CHRISTIAN; WEITZ, DAVID A.
To: PRESIDENT AND FELLOWS OF HARVARD COLLEGE
Reel/Frame 039669/0243 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2015
From: HUTCHISON, JOHN BRIAN, MR.
To: RAINDANCE TECHNOLOGIES, INC.
Reel/Frame 036789/0665 →
Continuity (3)
Continuation 12310048
Provisional Application 60836455 · Aug 7, 2006
Related Publication 20150217246A1 · Aug 6, 2015