Anionic water-soluble additives based on allyl ether and vinyl ether

1. An anionic modified copolymer obtained by polymerization of the monomers (A), (B) and (C) to obtain a nonionic copolymer having reactive terminal OH groups and conversion of the terminal OH groups to anionic end groups, wherein the anionic end groups are radicals SO 3 M, CH 2 COOM, PO 3 M 2 or sulfosuccinate, where M is H, a monovalent metal cation, a divalent metal cation, NH 4 + , a secondary, tertiary ammonium ion, quaternary ammonium ion or a combination thereof,

(A) is a monomer of formula (I)

wherein

A is C 2 - to C 4 -alkylene,

B is a C 2 - to C 4 -alkylene other than A,

k equals 0 or 1,

m is from 0 to 500,

n is from 0 to 500,

provided the sum total of m+n is from 1 to 1000;

wherein the monomer (B) is a compound of formula (IIa) or (IIb):

wherein

X a is an aromatic or araliphatic radical having 3 to 30 carbon atoms, optionally containing one or more of the heteroatoms N, O or S,

Z a is H or (C 1 -C 4 )-alkyl,

Z b is H or (C 1 -C 4 )-alkyl,

Z c is H or (C 1 -C 4 )-alkyl;

wherein

R 1 is hydrogen or methyl,

X b is an aromatic or araliphatic radical having 3 to 30 carbon atoms, optionally containing one or more of the heteroatoms N, O or S,

W a is oxygen or the NH; and

wherein the monomer (C) is a compound of formula (IIIa) or formula (IIIb):

wherein

R 2 is hydrogen or methyl,

Y is an aliphatic hydrocarbyl radical having 1 to 30 carbon atoms,

which optionally is linear or branched or cyclic, and optionally contains the heteroatoms O, N, S, or a combination thereof or optionally is unsaturated,

W b is oxygen or the NH;

wherein

R 3 is an aliphatic hydrocarbyl radical having 1 to 30 carbon atoms, which optionally is linear or branched or cyclic, and optionally contains the heteroatoms O, N, S or a combination thereof or is optionally unsaturated.

2. The copolymer as claimed in claim 1 , wherein the molar fraction of the monomers is 1 to 80% for monomer (A), 0.1 to 80% for monomer (B), and 0.1 to 80% for monomer (C).

3. The copolymer as claimed in claim 1 , wherein A is ethylene and B is propylene or A is propylene and B is ethylene.

4. The copolymer as claimed in claim 1 , wherein the copolymer is of the formulae (IV), (V), (VI) or (VII)

wherein

A is C 2 -C 4 -alkylene,

B is a C 2 -C 4 -alkylene other than A,

m is from 0 to 500,

n is from 0 to 500,

provided the sum total of m+n is from 1 to 1000,

X a is an aromatic or araliphatic radical having 3 to 30 carbon atoms optionally containing one or more of the heteroatoms N, O or S,

Z a is H or (C 1 -C 4 )-alkyl,

Z b is H or (C 1 -C 4 )-alkyl,

Z c is H or (C 1 -C 4 )-alkyl,

R 2 is hydrogen or methyl,

Y is an aliphatic hydrocarbyl radical having 1 to 30 carbon atoms, optionally linear or branched or cyclic, and optionally contains the heteroatoms O, N, or S, or is unsaturated,

W b is oxygen or an NH group,

R 1 is hydrogen or methyl,

X b is an aromatic or araliphatic radical having 3 to 30 carbon atoms, optionally containing one or more of the heteroatoms N, O or S,

W a is oxygen or an NH group,

R 3 is an aliphatic hydrocarbyl radical having 1 to 30 carbon atoms, optionally linear or branched or cyclic, and optionally contains heteroatoms O, N S and optionally is unsaturated

a=0.01 to 0.8; b=0.001 to 0.8; c=0.001 to 0.8

provided the sum total of a+b+c equals 1,

Q is SO 3 , CH 2 COO, PO 3 M or sulfosuccinate, where M is H, a monovalent metal cation, a divalent metal cation, NH 4 + , a secondary, tertiary or quaternary ammonium ion, or a combination thereof.

5. A process for preparing a copolymer as claimed in claim 1 , comprising the steps of free-radically polymerizing the monomers (A), (B) and (C) and converting the resulting terminal OH groups to anionic end groups.

6. A dispersant comprising a copolymer as claimed in claim 1 .

7. A pigment dispersant or filler dispersant comprising a copolymer as claimed in claim 1 .