Polymer dispersants

Patent metadata

Field	Value
Publication number	US-9670350-B2
Application number	US-201414896581-A
Country	US
Kind code	B2
Filing date	Jun 6, 2014
Priority date	Jun 7, 2013
Publication date	Jun 6, 2017
Grant date	Jun 6, 2017

Abstract

The present invention relates to novel polymer dispersants in the form of comb polymers P and to a liquid composition containing solid fine particles, such as organic or inorganic pigments and fillers, and the polymer dispersants. The comb polymer P having at least 0.5 mol-%, e.g. 0.5 to 90 mol-%, based on the total amount of repeating units in the comb polymer, of repeating units A, selected from repeating units of the formulae la and lb: wherein R 1 is selected from the group consisting of hydrogen, —S(═O) 2 R a , C 1 -C 20 alkyl, C 3 -C 10 cycloalkyl, aryl, heteroaryl, aryl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl; and X indicates a polymer group of the following formula X wherein Z indicates a polymer segment or a monovalent alkyl or alkenyl segment having from 10 to 100 carbon atoms; R1 is as defined above; k is 0, 1, 2, 3 or 4; n is 0, 1 or 2; A is a chemical bond or a divalent moiety selected from the group consisting of C 1 -C 6 alkylene, —O—(C 2 -C 6 alkylene) or —C(═O)—O—(C 2 -C 6 alkylene), where the C 2 -C 6 alkylene part is attached to Q; Q is a divalent moiety selected from the group consisting of —O—, —NH— and —S—; R 2 is independently selected from the group consisting of —OH, —COOH, —COOCH 3 , —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , —NO 2 , —S(═O) 2 R a , C 1 -C 20 alkyl, C 1 -C 4 alkoxy, halogen, aryloxy, aryl, heteroaryl.

First claim

We claim:

1. A comb polymer, comprising:
at least 0.5 mol %, based on a total amount of repeating units in the comb polymer, of a first repeating unit A, which is at least one selected from the group consisting of formula Ia and formula Ib:

wherein
R 1 is selected from the group consisting of a hydrogen, —S(═O) 2 R a , a C 1 -C 20 alkyl, a C 3 -C 10 cycloalkyl, an aryl, a heteroaryl, an aryl-C 1 -C 4 -alkyl and a heteroaryl-C 1 -C 4 -alkyl, where the aryl, the heteroaryl, the aryl-C 1 -C 4 -alkyl and the heteroaryl-C 1 -C 4 -alkyl are unsubstituted or substituted by at least one radical selected from the group consisting of —OH, —COOH, —COOCH 3 , —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , —NO 2 , —S(═O) 2 R a , a C 1 -C 4 alkyl, a C 1 -C 4 alkoxy and a halogen; and
X indicates a polymer group of the following formula X:

wherein
Z indicates a polymer segment, a monovalent alkyl group comprising 10 to 100 carbon atoms or an alkenyl group comprising 10 to 100 carbon atoms;
k is 0, 1, 2, 3 or 4;
n is 0, 1 or 2;
A is a chemical bond or a divalent moiety selected from the group consisting of a C 1 -C 6 alkylene, a —O—(C 2 -C 6 alkylene) and a —C(═O)—O—(C 2 -C 6 alkylene) which has the C 2 -C 6 alkylene part attached to Q;
Q is a divalent moiety selected from the group consisting of —O—, —NH— and —S—;
R 2 is independently selected from the group consisting of —OH, —COOH, —COOCH 3 , —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , —NO 2 , —S(═O) 2 R a , a C 1 -C 20 alkyl, a C 1 -C 4 alkoxy, a halogen, an aryloxy, an aryl, and a heteroaryl, where the aryl, the heteroaryl and the aryloxy are unsubstituted or substituted by at least one radical selected from the group consisting of —OH, —COOH, —COOCH 3 , —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , —NO 2 , —S(═O) 2 R a , a C 1 -C 4 alkyl, a C 1 -C 4 alkoxy and a halogen; and

wherein
R a is selected from the group consisting of —OH, —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , a C 1 -C 4 alkyl, a C 1 -C 4 alkoxy, an aryl and a heteroaryl, where the aryl and the hetaryl are unsubstituted or substituted by at least one radical selected from the group consisting of a C 1 -C 4 alkyl, a C 1 -C 4 alkoxy and a halogen.

2. The comb polymer of claim 1 , further comprising:
a second repeating unit of a polymerized monoethylenically unsaturated monomer, which is a neutral non-functional monoethylenically unsaturated monomer.

3. The comb polymer of claim 2 , wherein the second repeating unit is selected from the group consisting of a polymerized styrene, a C 4 -C 18 -olefin, and mixtures thereof.

4. The comb polymer of claim 2 , comprising:
0.5 mol % to 90 mol % of the first repeating unit;
10 mol % to 99.5 mol % of the second repeating unit; and further comprising:
0 mol % to 50 mol % of a third repeating unit, which is different from the first repeating unit and the second repeating unit;
wherein each amount is based on the total number of repeating units in the comb polymer.

5. The comb polymer of claim 1 , wherein
k is 0 or 1;
n is 0;
A is a chemical bond or a divalent moiety selected from the group consisting of —C(═O)—O—(C 2 -C 4 alkylene) which has the C 2 -C 4 alkylene part attached to Q and C(═O)—NH—(C 2 -C 4 alkylene) which has the C 2 -C 4 alkylene part attached to Q;
Q is a divalent moiety selected from the group consisting of —O— and —NH—;
R 1 is selected from the group consisting of a hydrogen, a C 1 -C 4 alkyl and a phenyl;
R 2 is independently selected from the group consisting of —OH, —COOH, —COOCH 3 , —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , —NO 2 , —S(═O) 2 R a , a C 1 -C 4 alkyl, a C 1 -C 4 alkoxy, a halogen, a phenyl and a pyridyl;
R a is selected from the group consisting of —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 and a C 1 -C 4 alkyl.

6. The comb polymer of claim 1 , wherein Z is selected from the group consisting of an alkyl group comprising 10 to 100 carbon atoms, an aliphatic polyester, an aliphatic polyether, an aliphatic polyether ester, an aliphatic polycarbonate and a polymer comprising:
a C-C-backbone; and
a C 1 -C 20 -alkoxycarbonyl moiety attached to the C-C-backbone.

7. The comb polymer of claim 6 , wherein Z is a poly-(C 2 -C 10 -alkylene oxide).

8. The comb polymer of claim 6 , wherein Z is an aliphatic polyester or an aliphatic polyether ester.

9. The comb polymer of claim 6 , wherein Z is an aliphatic polycarbonate.

10. The comb polymer of claim 6 , wherein Z is a polymer segment comprising:
a C—C-backbone, and
a fourth repeating unit, which is a polymerized C 1 -C 20 -alkyl (meth)acrylate.

11. The comb polymer of claim 1 , wherein Z is a polymer segment which has a number average weight in a range of 200 Dalton to 50000 Dalton.

12. The comb polymer of claim 1 , further comprising:
a fifth repeating unit a formula selected from the group consisting of formula C-1, formula C-2, formula C-3, formula C-4, formula C-5 and mixtures thereof:

where
R 3 , R 8 are each independently a hydrogen or a monovalent hydrocarbon radical comprising 1 to 24 carbon atoms;
R 4 is a bivalent alkandiyl radical comprising 2 to 24 carbon atoms;
R 5 , R 6 , R 7 are identical or different and selected from the group consisting of an alkyl comprising 1 to 15 carbon atoms, a cycloalkyl comprising 6 to 12 carbon atoms, a substituted or an unsubstituted aryl and a substituted or an unsubstituted aryl-C 1 -C 4 -alkyl, where at least one of R 5 , R 6 , R 7 is optionally hydrogen, and
R 9 is a bivalent radical selected from the group consisting of an alkandiyl radical comprising 2 to 24 carbon atoms and an O-alkandiyl radical comprising 2 to 24 carbon atoms, where the O-alkandiyl radical comprises an oxygen atom bound to the phosphorus atom.

13. A process for preparing the comb polymer of claim 1 , the process comprising:
reacting a first polymer comprising at least 0.5 mol %, based on the total amount of repeating units in the first polymer, of a repeating unit of polymerized maleic anhydride with a polymer of formula II:

to obtain a precursor comb polymer to the comb polymer.

14. The process of claim 13 , wherein the first polymer is a copolymer of styrene and maleic anhydride.

15. The process of claim 13 , further comprising:
performing at least one reaction selected from the group consisting of:
reacting the precursor comb polymer with water and optionally subsequent neutralization;
reacting the precursor comb polymer with a diamine of formula R 3 NH—R 4 —NR 5 R 6 , followed by quaternization, where
R 3 is a hydrogen or a monovalent hydrocarbon radical comprising 1 to 24 carbon atoms;
R 4 is a bivalent alkandiyl radical comprising 2 to 24 carbon atoms;
R 5 and R 6 are identical or different and selected from the group consisting of an alkyl comprising 1 to 15 carbon atoms, a cycloalkyl comprising 6 to 12 carbon atoms, a substituted or an unsubstituted aryl and a substituted or an unsubstituted aryl-C 1 -C 4 -alkyl, where at least one of R 5 and R 6 is optionally a hydrogen;
reacti

Assignees

• Basf Se

Inventors

• Kou Huiguang
• Auschra Clemens
• Pirrung Frank
• Maier Matthias
• Perera-Diez Dario

Classifications

• C08F212/08

  Styrene · CPC title

• C08F8/32

  by reaction with amines · CPC title

• C09D11/10 Primary

  based on artificial resins · CPC title

• C09D125/14

  with unsaturated esters · CPC title

• C08L25/14 Primary

  with unsaturated esters · CPC title