Granted Patent B2

US 12,606,747 · App. 17/922,283 · Granted Apr 21, 2026

Inventors: Xin Li (Cambridgeshire, GB); Clive Smith (Cambridgeshire, GB); Ben Mackworth (Cambridgeshire, GB)

Assignee: Sphere Fluidics Limited

C09K23/42

Abstract

Claims (103)

1 . A surfactant of formula (I):

(A) m -X—(B) n   (I)

wherein

X is a linking group;

each A is independently a fluorocarbon or a perfluoropolyether;

each B is independently

wherein a is an integer between 3 and 50 and each R is independently C 1-6 alkyl, CH 2 CH 2 OC 1-6 alkyl or CH 2 CH(CH 3 )OC 1-6 alkyl;

m is an integer between 1 and 10; and

n is an integer between 1 and 10.

2 . A surfactant as claimed in claim 1 , which is a star surfactant.

3 . A surfactant as claimed in claim 1 , wherein the sum of n and m is an integer between 3 and 10.

4 . A surfactant as claimed in claim 1 , wherein the sum of n and m is 3, 4, 5, 6 or 7.

5 . A surfactant as claimed in claim 1 , wherein a is an integer between 3 and 24.

6 . A surfactant as claimed in claim 1 , wherein each R is C 1-6 alkyl.

7 . A surfactant as claimed in claim 1 , wherein n is an integer between 1 and 6.

8 . A surfactant as claimed in claim 1 , wherein m is 1, 2 or 3.

9 . A surfactant as claimed in claim 1 , wherein at least one A is a perfluoropolyether.

10 . A surfactant as claimed in claim 1 , wherein said perfluoropolyether comprises a repeat unit of the formula:

−[CF(CF 3 )CF 2 O] b —,

wherein b is a positive integer.

11 . A surfactant as claimed in claim 1 , wherein said linking group comprises a group selected from —C(O)NH—, —C(O)NMe-, —NHC(O)—, —NMeC(O)—, —C(O)S—, —SC(O)—, —C(O)O—, —OC(O)—, —OC(O)O—, —OC(O)NH—, —OC(O)NMe-, —O—, —S—, —NHC(O)NH—, —NMeC(O)NH—, —NHC(O)NMe-, —NHC(O)O—, —NMeC(O)O—, —SO 2 NH—, —NHSO 2 —, —NHSO 2 —C 6 H 4 —O— and —O—C 6 H 4 —SO 2 NH.

12 . A surfactant as claimed in claim 1 , wherein said linking group comprises a charged group.

13 . A surfactant as claimed in claim 1 , wherein said linking group comprises a group selected from:

wherein

R 1 and R 2 are independently selected from H and C 1-6 alkyl; and

W − is a counter ion.

14 . A surfactant as claimed in claim 1 , wherein said linking group comprises a heterocycle and/or a C 1-6 alkylene group, or consists of a C 1-6 alkylene group.

15 . A surfactant as claimed in claim 1 , wherein said linking group comprises a group selected from:

wherein

each p is independently 0 or an integer between 1 and 6;

each q is independently 0 or an integer between 1 and 6;

each r is independently an integer between 1 and 6;

s is an integer between 1 and 6;

each Z is independently selected from C(O)NH, C(O)NMe, NHC(O), NMeC(O), OC(O)NH, C(O)O, —NHC(O)O—, —NMeC(O)O— or O;

each U is independently a heterocycle; and

each Y is independently selected from

wherein W, R 1 and R 2 are as defined in claim 13 .

16 . A surfactant as claimed in claim 1 , wherein said linking group is of formula (IIa), (IIb), (IIc) or (IId):

wherein

p is 0 or 1;

q is 0, 1 or 2; and

Z is selected from C(O)NH, C(O)NMe, NHC(O), NMeC(O), OC(O)NH, C(O)O, —NHC(O)O—, —NMeC(O)O— or O;

or said linking group is of formula (IIIe), (IIIf) or (IIIg):

wherein

p is 0 or 1;

q is 0, 1 or 2;

r is an integer between 1 and 6;

Z is selected from C(O)NH, C(O)NMe, NHC(O), NMeC(O), OC(O)NH, C(O)O, —NHC(O)O—, —NMeC(O)O— or O;

Y is selected from

wherein W, R 1 and R 2 are as defined in claim 13 ;

or said linking group is of formula (IIIh), (IIIi) or (IIIj)

wherein

p is 0 or 1;

q is 0, 1 or 2;

r is an integer between 1 and 6;

Z is selected from C(O)NH, C(O)NMe, NHC(O), NMeC(O), OC(O)NH, C(O)O, —NHC(O)O—, —NMeC(O)O— or O; and

U is a heterocycle;

or said linking group is of formula (IIIk):

wherein

each p is 0 or 1;

each q is 0, 1 or 2; and

each Z is independently selected from C(O)NH, C(O)NMe, NHC(O), NMeC(O), OC(O)NH, C(O)O, —NHC(O)O—, —NMeC(O)O— or O;

or said linking group is of formula (IIIl) or (IIIm):

wherein

each p is 0 or 1;

each q is 0, 1 or 2;

® each r is an integer between 1 and 6;

each Z is independently selected from C(O)NH, C(O)NMe, NHC(O), NMeC(O), OC(O)NH, C(O)O, —NHC(O)O—, —NMeC(O)O— or O;

each U is a heterocycle; and

each Y is independently selected from:

wherein W, R 1 and R 2 are as defined in claim 13 ;

or said linking group is of formula (IIIn):

wherein

each p is 0 or 1;

each q is 0, 1 or 2;

each r is an integer between 1 and 6;

s is an integer between 1 and 6;

each Z is independently selected from C(O)NH, C(O)NMe, NHC(O), NMeC(O), OC(O)NH, C(O)O, —NHC(O)O—, —NMeC(O)O— or O; and

each Y is independently selected from:

wherein W, R 1 and R 2 are as defined in claim 13 ;

or said linking group is of formula IIIo, IIIp, or IIIq

wherein

each p is independently 0 or an integer between 1 and 6;

each q is independently 0 or an integer between 1 and 6; and

each Z is independently selected from C(O)NH, C(O)NMe, NHC(O), NMeC(O), OC(O)NHI, C(O)O, —NHC(O)O—, —NMeC(O)O— or O.

17 . A surfactant as claimed in claim 1 , wherein the ratio of the number of atoms in the linking group, excluding hydrogen and halogen atoms, as well as any atoms on side or branch groups, to the total number of atoms in the groups A and B, excluding hydrogen and halogen atoms, as well as any atoms on side or branch groups, is 1:2 to 1:500.

18 . A surfactant as claimed in claim 1 is selected from the group consisting of:

wherein a is an integer between 3 and 50; and b is a positive integer.

19 . A method for making a surfactant as claimed in claim 1 comprising:

reacting a compound of formula (II)

(A) m -X—(OH) n   (II)

wherein

X is a linking group;

each A is independently a fluorocarbon or a perfluoropolyether;

m is an integer between 1 and 10;

n is an integer between 1 and 10;

with a compound of formula (III)

wherein each R is independently C 1-6 alkyl, CH 2 CH 2 OC 1-6 alkyl or CH 2 CH(CH 3 )OC 1-6 alkyl;

or

reacting a compound comprising (A) m with a compound comprising (B) n , wherein said reaction is a coupling reaction and forms linker X between said (A) m and said (B) n .

20 . A composition, comprising a surfactant of formula (I) as claimed in claim 1 .

21 . A composition as claimed in claim 20 , wherein the composition is an emulsion, and wherein said emulsion comprises a continuous oil phase and a discontinuous aqueous phase.

22 . A method comprising performing one or more chemical and/or biological reactions, and/or biological processes in the discontinuous aqueous phase of an emulsion as claimed in claim 21 .

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (60)