Polymer dispersants

Patent metadata

Field	Value
Publication number	US-9404009-B2
Application number	US-201314380557-A
Country	US
Kind code	B2
Filing date	Feb 22, 2013
Priority date	Feb 24, 2012
Publication date	Aug 2, 2016
Grant date	Aug 2, 2016

Abstract

The present invention relates to novel polymer dispersants and to a liquid compositions containing solid fine particles, such as organic or inorganic pigments and fillers, and the polymer dispersants. The polymer dispersants have at least one functional moiety of the formula I, which is bound to one of the termini or to the backbone of the polymer: (I) where # indicates the point of attachment to the terminus and/or to the polymer backbone; k is 0, 1, 2, 3 or 4, m is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, 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), —C(═O—O—(C 2 -C 6 alkylene), —NR 3 —(C 2 -C 6 alkylene) and C(═O)—NR 3 —(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 1 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 4 , C 1 -C 20 alkyl, C 1 -C 4 alkoxy, halogen, aryloxy, aryl, heteroaryl; R 2 is selected from the group consisting of hydrogen, —S(═O) 2 R 4 , 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; R 3 is selected from the group consisting of hydrogen, —S(═O) 2 R 4 , C 1 -C 20 alkyl, C 3 -C 10 cycloalkyl, aryl and heteroaryl; R 4 is selected from the group consisting of OH, —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy, aryl and heteroaryl.

First claim

We claim:

1. A liquid composition comprising a fine particulate solid material, a liquid diluent, and a polymer P, said polymer comprising at least one functional group of formula I:

bound to one of the termini and/or to the backbone of the polymer, where
# indicates the point of attachment to the terminus and/or to the polymer backbone;
k is 0, 1, 2, 3 or 4;
m is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
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), —C(═O)—O—(C 2 -C 6 alkylene), —NR 3 —(C 2 -C 6 alkylene) and C(═O)—NR 3 —(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 1 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 4 , C 1 -C 20 alkyl, C 1 -C 4 alkoxy, halogen, aryloxy, aryl, and heteroaryl, where aryl, heteroaryl and aryloxy are unsubstituted or substituted by 1, 2, 3 or 4 radicals 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 4 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halogen;
R 2 is selected from the group consisting of hydrogen, —S(═O) 2 R 4 , 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, where aryl, heteroaryl, aryl-C1-C4-alkyl and heteroaryl-C1-C4-alkyl are unsubstituted or substituted by 1, 2, 3 or 4 radicals 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 4 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halogen;
R 3 is selected from the group consisting of hydrogen, —S(═O) 2 R 4 , C 1 -C 20 alkyl, C 3 -C 10 cycloalkyl, aryl and heteroaryl, where aryl and heteroaryl are unsubstituted or substituted by 1, 2, 3 or 4 radicals 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 4 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halogen;
R 4 is selected from the group consisting of OH, —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy, aryl and heteroaryl, where aryl and heteroaryl are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halogen, and
polymer P is selected from the group consisting of aliphatic polyesters, aliphatic polyethers, aliphatic polyetheresters, aliphatic polycarbonates and polymers having a C—C-backbone that comprises repeating units M1 selected from polymerized C 1 -C 10 -alkyl(meth)acrylates, polymerized C 1 -C 10 -alkyl-(poly-C 2 -C 4 -alkyleneglycol)(meth)acrylates and polymerized vinylaromatic hydrocarbon compounds.

2. The composition according to claim 1 , wherein
k is 0 or 1;
m is 0 or 1;
A is a chemical bond or a divalent moiety selected from the group consisting of —C(═O)—O—(C 2 -C 4 alkylene) and C(═O)—NH—(C 2 -C 4 alkylene), where the alkylene part is attached to Q;
Q is a divalent moiety selected from the group consisting of —O— and —NH—;
R 1 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 4 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, phenyl and pyridyl;
R 2 is selected from the group consisting of hydrogen, C 1 -C 4 alkyl and phenyl;
R 4 is selected from the group consisting of —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 and C 1 -C 4 alkyl.

3. A liquid composition comprising a fine particulate solid material, a liquid diluent, and a polymer P, said polymer comprising at least one functional group of formula I:

bound to one of the termini and/or to the backbone of the polymer, where
# indicates the point of attachment to the terminus and/or to the polymer backbone;
k is 0, 1, 2, 3 or 4;
m is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9;
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), —C(═O)—O—(C 2 -C 6 alkylene), —NR 3 —(C 2 -C 6 alkylene) and C(═O)—NR 3 —(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 1 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 4 , C 1 -C 20 alkyl, C 1 -C 4 alkoxy, halogen, aryloxy, aryl, and heteroaryl, where aryl, heteroaryl and aryloxy are unsubstituted or substituted by 1, 2, 3 or 4 radicals 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 4 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halogen;
R 2 is selected from the group consisting of hydrogen, —S(═O) 2 R 4 , 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, where aryl, heteroaryl, aryl-C1-C4-alkyl and heteroaryl-C1-C4-alkyl are unsubstituted or substituted by 1, 2, 3 or 4 radicals 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 4 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halogen;
R 3 is selected from the group consisting of hydrogen, —S(═O) 2 R 4 , C 1 -C 20 alkyl, C 3 -C 10 cycloalkyl, aryl and heteroaryl, where aryl and heteroaryl are unsubstituted or substituted by 1, 2, 3 or 4 radicals 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 4 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halogen;
R 4 is selected from the group consisting of OH, —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 -C 6 alkyl) 2 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy, aryl and heteroaryl, where aryl and heteroaryl are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy and halogen, and
polymer P is a poly-(C 2 -C 4 -alkylene oxide).

4. The composition according to claim 1 wherein the polymer P is an aliphatic polyester.

5. The composition according to claim 1 wherein the polymer P is an aliphatic polyetherester.

6. The composition according to claim 1 wherein the polymer P is an aliphatic polycarbonate.

7. The composition according to claim 1 , where the polymer P has a C—C backbone which comprises repeating units M1, selected from polymerized C 1 -C 10 -alkyl(meth)acrylates, polymerized C 1 -C 10 -alkyl-(poly-C 2 -C 4 -alkyleneglycol)(meth)acrylates and polymerized vinyl aromatic hydrocarbon compounds.

8. The composition according to claim 1 wherein the polymer P has a number average weight of from 250 to 100,000 Dalton.

9. The composition according to claim 1 , wherein polymer P is obtained by reacting a polymer P′ having at least one functional moiety of the formula A-Q-H attached to one of the termini and/or to the backbone of the polymer P′ with a compound of the formulae II, II′ or III

R L is hydrogen or a hydrocarbon radical having from 1 to 8 carbon atoms and

Assignees

• Basf Se

Inventors

• Kou Huiguang
• Auschra Clemens
• Pirrung Frank

Classifications

• C08G63/6852

  derived from hydroxy carboxylic acids · CPC title

• C09D133/08 Primary

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C08G64/42

  Chemical after-treatment · CPC title

• C09D17/00

  Pigment pastes, e.g. for mixing in paints (artists' paints C09D5/06) · CPC title

• C08G63/912

  derived from hydroxycarboxylic acids · CPC title