Ethanolamine Glyceryl Ethers

1 . A process for modifying the interfacial activity of a substance, comprising the step of adding at least one ethanolamine glyceryl ether condensation product of the formula (I)

wherein

R 1 , R 2 and R 3 , in each case independently of one another, may be identical or different and

are hydrogen,

are a linear or branched, saturated alkyl chain having 1 to 20 carbon atoms,

are a linear or branched unsaturated alkenyl group having 2 to 20 carbon atoms,

are —CH 2 —CH 2 —OH or

are a radical of the formula (II)

wherein

(O-A) is an alkyleneoxy group selected from ethyleneoxy group (EO), propyleneoxy group (PO), butyleneoxy group and/or phenyloxirane group,

a is a number from 0 to 50,

b is a number from 0 to 50,

R 5 is hydrogen and/or

is (O-A) a H, wherein (O-A) is an alkyleneoxy group selected from the group consisting of: ethyleneoxy group (EO), propyleneoxy group (PO), butyleneoxy group and phenyloxirane group and a is a number from 1 to 30, and/or

is —(CR 6 R 7 ) a -phenyl, where R 6 and R 7 , which may be identical or different, are —H, are an OH group, are a linear or branched (C 1 -C 10 )-alkyl or are a linear or branched (C 2 -C 30 )-alkenyl and a is a number from 1 to 10, and/or

is —(CR 6 R 7 ) a -naphthyl, where R 6 and R 7 , which may be identical or different, are —H, are an OH group, are a linear or branched (C 1 -C 10 )-alkyl or are a linear or branched (C 2 -C 30 )-alkenyl and a is a number from 1 to 10, and/or

is a group of the formula (III)

and/or

is R 8 R 9 N—(CH 2 ) b —, where R 8 and R 9 , which may be identical or different, are —H, linear or branched (C 1 -C 10 )-alkyl or linear or branched (C 2 -C 30 )-alkenyl and b is a number from 1 to 22, and/or

is HO—(CH 2 ) b —, where b is a number from 1 to 22, and/or

is —SO 3 − X + , —PO 3 2− X + X′ + or —CH 2 COO − X + , where X + and X′ + are H + , Li + , Na + , K + , Ca 2+ /2, Mg 2+ /2 or N(R 8 ) 4 + and the R 8 may be identical or different and are —H or (C 1 -C 10 )-alkyl, and/or

is a group of the formula (IV)

wherein

X + and X′ + are H + , Li + , Na + , K + , Ca 2+ /2, Mg 2+ /2 or N(R 8 ) 4 + , and the R 8 may be identical or different and are —H or (C 1 -C 10 )-alkyl, and/or

is —C(R 11 ) 2 —COO − X + , —CO—R 12 —COO − X + or

—C(R 11 ) 2 C(R 11 ) 2 C(R 11 ) 2 —N(R 13 ) 2 , where the R 11 may be identical or different and are —H and/or CH 3 , R 12 is (C 1 -C 10 )-alkylene or (C 2 -C 30 )-alkenylene, the R 13 may be identical or different and are (C 1 -C 10 )-alkyl or (C 2 -C 30 )-alkenyl, X + is H + , Li + , Na + , K + , Ca 2+ /2, Mg 2+ /2 or N(R 8 ) 4 + , and the R 8 may be identical or different and are —H or (C 1 -C 10 )-alkyl, and/or

is —C(R 14 ) 2 C(R 14 ) 2 C(R 14 ) 2 —N((GO) z H) 2 , where the R 14 may be identical or different and are —H and/or —CH 3 , G is —C 2 H 4 —, —C 3 H 6 — or —C 4 H 8 — and z is a number from 1 to 22, and/or

is a group of the formula (V)

c is a number from 1 to 25,

(O-D) is an alkyleneoxy group selected from ethyleneoxy group (EO), propyleneoxy group (PO), butyleneoxy group and/or phenyloxirane group,

d is a number from 0 to 50,

e is a number from 0 to 50, and

R 4 can have the meaning of R 5 ,

with the proviso that at least one of the radicals R 1 , R 2 and R 3 is a radical of the formula (II) and at least one of the other radicals R 1 , R 2 and R 3 is selected from —CH 2 —CH 2 —OH and radicals of the formula (II)

to a dispersion.

2 . The process as claimed in claim 1 , wherein, in the at least one ethanolamine glyceryl ether condensation product, at least two of the radicals R 1 , R 2 and R 3 are radicals of the formula (II).

3 . The process as claimed in claim 1 , wherein, in the at least one ethanolamine glyceryl ether condensation product, two of the radicals R 1 , R 2 and R 3 are radicals of the formula (II).

4 . The process as claimed in claim 3 , wherein, in the at least one ethanolamine glyceryl ether condensation product, the third of the radicals R 1 , R 2 and R 3 is a linear or branched, saturated alkyl chain having 1 to 20, carbon atoms or is a linear or branched unsaturated alkenyl group having 2 to 20 carbon atoms.

5 . The process as claimed in claim 4 , wherein, in the at least one ethanolamine glyceryl ether condensation product, the third of the radicals R 1 , R 2 and R 3 is a linear or branched, saturated alkyl chain having 1 to 20 carbon atoms.

6 . The process as claimed in claim 1 , wherein, in the at least one ethanolamine glyceryl ether condensation product, all three radicals R 1 , R 2 and R 3 are selected from the group consisting of CH 2 —H 2 —OH and radicals of the formula (II).

7 . The process as claimed in claim 6 , wherein, in the at least one ethanolamine glyceryl ether condensation product, all three radicals R 1 , R 2 and R 3 are radicals of the formula (II).

8 . The process as claimed in claim 1 , wherein, in the at least one ethanolamine glyceryl ether condensation product, (O-A) and (O-D) are in each case a uniform alkyleneoxy group, (a+b) is a number from 0 to 20 and (d+e) is a number from 0 to 20.

9 . The process as claimed in claim 1 , wherein, in the at least one ethanolamine glyceryl ether condensation product, (O-A) (a+b) and (O-D) (d+e) are mixed alkyleneoxy groups of the formula —(O-A 1 ) a -(O-A 2 ) b - or —(O-D 1 ) d -(O-D 2 ) e -, which may be arranged randomly or blockwise, and in which a and b are in each case a number from 1 to 30, and d and e are in each case a number from 1 to 20, (O-A 1 ) and (O-D 1 ) are an ethyleneoxy unit, and (O-A 2 ) and (O-D 2 ) are a propyleneoxy unit, a butyleneoxy unit, a phenyloxirane unit, or mixtures of these.

10 . The process as claimed claim 1 , wherein, in the at least one ethanolamine glyceryl ether condensation product, the radicals R 1 , R 2 and R 3 are identical and are a group of the formula (IIa),

wherein

R 5 is hydrogen,

c is a number from 1 to 25, and

R 4 is hydrogen.

11 . The process as claimed claim 1 , wherein, in the at least one ethanolamine glyceryl ether condensation product, the radicals R 1 , R 2 and R 3 are identical and are a group of the formula (IIa),

wherein

R 5 is hydrogen,

c is a number from 1 to 25, and

R 4 is a group of the formula (III)

12 . The process as claimed claim 1 , wherein, in the at least one ethanolamine glyceryl ether condensation product, the radicals R 1 , R 2 and R 3 are identical and are a group of the formula (IIb),

wherein

(O-A) (a+b) is a uniform alkyleneoxy group and (a+b) is a number from 1 to 50 or is a mixed alkyleneoxy group of the formula -(O-A 1 ) a -(O-A 2 ) b -, which can be arranged randomly or blockwise and in which (a+b) is a number from 1 to 50, (O-A 1 ) is an ethyleneoxy unit and (O-A 2 ) is a propyleneoxy unit, a butyleneoxy unit, a phenyloxirane unit or mixtures of these,

R 5 is hydrogen,

c is a number from 1 to 25, and

R 4 is hydrogen.

13 . The process as claimed in claim 1 , wherein, in the at least one ethanolamine glyceryl ether condensation products, the radicals R 1 , R 2 and R 3 are identical and are a group of the formula (IIc),

in which

(O-A) is an alkyleneoxy group,

a is a number from 1 to 50,

R 5 is hydrogen,

c is a number from 1 to 25, and

R 4 is hydrogen.

14 . The process as claimed in claim 1 , wherein, in the at least one ethanolamine glyceryl ether condensation product,

R 1 is an alkyl group having 1 to 20, carbon atoms, and

R 2 and R 3 are identical and are a group of the formula (IId)

wherein

R 5 is hydrogen,

c is a number from 1 to 25, and

R 4 is hydrogen.

15 . The process as claimed in claim 1 , wherein, in the at least one ethanolamine glyceryl ether condensation product,

R 1 is an alkyl group having 1 to 10 carbon atoms, and

R 2 and R 3 are identical and are a group of the formula (IId)

wherein

R 5 is hydrogen,

c is a number from 1 to 25, and

R 4 is hydrogen.

16 . (canceled)

17 . An ethanolamine glyceryl ether condensation product of the formula (I)

wherein

R 1 , R 2 and R 3 , in each case independently of one another, may be identical or different and

are hydrogen,

are a linear or branched, saturated alkyl chain having 1 to 20 carbon atoms,

are a linear or branched unsaturated alkenyl group having 2 to 20 carbon atoms,

are —CH 2 —CH 2 —OH or

are a radical of the formula (II)

wherein

(O-A) is an alkyleneoxy group selected from the group consisting of: ethyleneoxy group (EO), propyleneoxy group (PO), butyleneoxy group and phenyloxirane group,

a is a number from 0 to 50,

b is a number from 0 to 50,

R 5 is hydrogen and/or

is (O-A) a H, in which (O-A) is an alkyleneoxy group selected from the group consisting of: ethyleneoxy group (EO), propyleneoxy group (PO), butyleneoxy group and phenyloxirane group and a is a number from 1 to 30, and/or

is —(CR 6 R 7 ) a -phenyl, where R 6 and R 7 , which may be identical or different, are —H, are an OH group, are a linear or branched (C 1 -C 10 )-alkyl or are a linear or branched (C 2 -C 30 )-alkenyl and a is a number from 1 to 10, and/or

is —(CR 6 R 7 ) a -naphthyl, where R 6 and R 7 , which may be identical or different, are —H, are an OH group, are a linear or branched (C 1 -C 10 )-alkyl or are a linear or branched (C 2 -C 30 )-alkenyl and a is a number from 1 to 10, and/or is a group of the formula (III)

and/or

is R 8 R 9 N—(CH 2 ) b —, where R 8 and R 9 , which may be identical or different, are —H, linear or branched (C 1 -C 10 )-alkyl or linear or branched (C 2 -C 30 )-alkenyl and b is a number from 1 to 22, and/or

is HO—(CH 2 ) b —, where b is a number from 1 to 22, and/or

is —SO 3 − X + , —PO 3 2− X + X′ + or —CH 2 COO − X + , where X + and X′ + are H + , Li + , Na + , K + , Ca 2+ /2, Mg 2+ /2 or N(R 8 ) 4 + and the R 8 may be identical or different and are —H or (C 1 -C 10 )-alkyl, and/or

is a group of the formula (IV)

wherein

X + and X′ + are H + , Li + , Na + , K + , Ca 2+ /2, Mg 2+ /2 or N(R 8 ) 4 + , and the R 8 may be identical or different and are —H or (C 1 -C 10 )-alkyl, and/or

is —C(R 11 ) 2 —COO − X + , —CO—R 12 —COO − X + or —C(R 11 ) 2 C(R 11 ) 2 C(R 11 ) 2 —N(R 13 ) 2 , where the R 11 may be identical or different and are —H and/or CH 3 , R 12 is (C 1 -C 10 )-alkylene or (C 2 -C 30 )-alkenylene, the R 13 may be identical or different and are (C 1 -C 10 )-alkyl or (C 2 -C 30 )-alkenyl, X + is H + , Li + , Na + , K + , Ca 2+ /2, Mg 2+ /2 or N(R 8 ) 4 + , and the R 8 may be identical or different and are —H or (C 1 -C 10 )-alkyl, and/or

is —C(R 14 ) 2 C(R 14 ) 2 C(R 14 ) 2 —N((Go) Z H) 2 , where the R 14 may be identical or different and are —H and/or —CH 3 , G is —C 2 H 4 —, —C 3 H 6 — or —C 4 H 8 — and z is a number from 1 to 22, and/or

is a group of the formula (V)

c is a number from 1 to 25,

(O-D) is an alkyleneoxy group selected from the group consisting of: ethyleneoxy group (EO), propyleneoxy group (PO), butyleneoxy group and phenyloxirane group,

d is a number from 0 to 50,

e is a number from 0 to 50, and

R 4 can have the meaning of R 5 ,

with the proviso that at least two of the radicals R 1 , R 2 and R 3 are radicals of the formula (II) and at least one of the other radicals R 1 , R 2 and R 3 is selected from the group consisting of —CH 2 —CH 2 —OH and radicals of the formula (II).

18 . An ethanolamine glyceryl ether condensation product as claimed in claim 17 , wherein two of the radicals R 1 , R 2 and R 3 are radicals of the formula (II).

19 . An ethanolamine glyceryl ether condensation product as claimed in claim 18 , wherein the third of the radicals R 1 , R 2 and R 3 is a linear or branched, saturated alkyl chain having 1 to 20, carbon atoms or is a linear or branched unsaturated alkenyl group having 2 to 20, carbon atoms.

20 . An ethanolamine glyceryl ether condensation product as claimed in claim 19 , wherein the third of the radicals R 1 , R 2 and R 3 is a linear or branched, saturated alkyl chain having 1 to 20 carbon atoms.

21 . An ethanolamine glyceryl ether condensation product as claimed in claim 17 , wherein all three radicals R 1 , R 2 and R 3 are selected from the group consisting of CH 2 —H 2 —OH and radicals of the formula (II).

22 . An ethanolamine glyceryl ether condensation product as claimed in claim 21 , wherein all three radicals R 1 , R 2 and R 3 are radicals of the formula (II).

23 . An ethanolamine glyceryl ether condensation product as claimed in claim 17 , wherein (O-A) and (O-D) are in each case a uniform alkyleneoxy group, (a+b) is a number from 0 to 20 and (d+e) is a number from 0 to 20.

24 . An ethanolamine glyceryl ether condensation product as claimed in claim 17 , wherein (O-A) (a+b) and (O-D) (d+e) are mixed alkyleneoxy groups of the formula —(O-A 1 ) a -(O-A 2 ) b - or —(O-D 1 ) d -(O-D 2 ) e -, which may be arranged randomly or blockwise, and in which a and b are in each case a number from 1 to 30, and d and e are in each case a number from 1 to 20, (O-A 1 ) and (O-D 1 ) are an ethyleneoxy unit, and (O-A 2 ) and (O-D 2 ) are a propyleneoxy unit, a butyleneoxy unit, a phenyloxirane unit, or mixtures of these.

25 . An ethanolamine glyceryl ether condensation product as claimed in claim 17 , wherein the radicals R 1 , R 2 and R 3 are identical and are a group of the formula (IIa),

wherein

R 5 is hydrogen,

c is a number from 1 to 25, and

R 4 is hydrogen.

26 . An ethanolamine glyceryl ether condensation product as claimed in claim 17 , wherein the radicals R 1 , R 2 and R 3 are identical and are a group of the formula (IIa),

wherein

R 5 is hydrogen,

c is a number from 1 to 25, and

R 4 is a group of the formula (III)

27 . An ethanolamine glyceryl ether condensation product as claimed in claim 17 , wherein the radicals R 1 , R 2 and R 3 are identical and are a group of the formula (IIb)

wherein

(O-A) (a+b) is a uniform alkyleneoxy group and (a+b) is a number from 1 to 50 or is a mixed alkyleneoxy group of the formula -(O-A 1 ) a -(O-A 2 ) b -, which can be arranged randomly or blockwise and in which (a+b) is a number from 1 to 50, (O-A 1 ) is an ethyleneoxy unit and (O-A 2 ) is a propyleneoxy unit, a butyleneoxy unit, a phenyloxirane unit or mixtures of these,

R 5 is hydrogen,

c is a number from 1 to 25, and

R 4 is hydrogen.

28 . An ethanolamine glyceryl ether condensation product as claimed in claim 17 , wherein the radicals R 1 , R 2 and R 3 are identical and are a group of the formula (IIc)

wherein

(O-A) is an alkyleneoxy group,

a is a number from 1 to 50,

R 5 is hydrogen,

c is a number from 1 to 25, and

R 4 is hydrogen.

29 . An ethanolamine glyceryl ether condensation product as claimed in claim 17 , wherein

R 1 is an alkyl group having 1 to 20, carbon atoms, and

R 2 and R 3 are identical and are a group of the formula (IId)

wherein

R 5 is hydrogen,

c is a number from 1 to 25, and

R 4 is hydrogen.

30 . An ethanolamine glyceryl ether condensation product as claimed in claim 17 , wherein

R 1 is an alkyl group having 1 to 10 carbon atoms, and

R 2 and R 3 are identical and are a group of the formula (IId)

wherein

R 5 is hydrogen,

c is a number from 1 to 25, and

R 4 is hydrogen.

31 . A dispersion comprising at least one ethanolamine glyceryl ether condensation products as claimed in claim 17 .