Polymers and use of these as dispersants

Patent metadata

Field	Value
Publication number	US-9701785-B2
Application number	US-201414903253-A
Country	US
Kind code	B2
Filing date	Jul 21, 2014
Priority date	Jul 22, 2013
Publication date	Jul 11, 2017
Grant date	Jul 11, 2017

Abstract

A polymer comprises at least one functional group of the formula (I) bound to one of the termini and/or to the backbone of the polymer, or a salt thereof. # indicates the point of attachment to the terminus and/or to the polymer backbone; 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—; and X is a divalent moiety selected from the group consisting of linear C 1 -C 10 alkylene, linear C 2 -C 6 alkenylene, C 4 -C 7 cycloalkylene, arylene and alkarylene, wherein the linear C 1 -C 10 alkylene, the linear C 2 -C 6 alkenylene, the C 4 -C 7 cycloalkylene, the arylene and the alkarylene may be substituted.

First claim

We claim:

1. A polymer P comprising at least one functional group of the formula (I):

bound to one of the termini and/or to the backbone of the polymer, or a salt thereof,
wherein:
# 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(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, where aryl, hetaryl 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 and hetaryl in the four last mentioned radicals 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;
X is a divalent moiety selected from the group consisting of linear C 1 -C 10 alkylene, linear C 2 -C 6 alkenylene, C 4 -C 7 cycloalkylene, arylene and alkarylene, where the linear C 1 -C 10 alkylene, linear C 2 -C 6 alkenylene and C 4 -C 7 cycloalkylene are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of C 1 -C 18 alkyl or C 1 -C 18 alkenyl, and where arylene and alkarylene 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 haloalkyl, aryl, —COOH, —COOCH 3 , —NO 2 or 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 hetaryl 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 hetaryl 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;
Y is selected from —OH or a moiety of the general formula (I.2):

where * indicates the point of attachment to the carbonyl group and #, k, m, A, Q, R 1 and R 2 are as defined above; and
the polymer P is selected from the group consisting of a polyester, a polyether, a polyetherester, a polycarbonate and a polymer having a C—C-backbone, in which the polymer having a C—C-backbone comprises repeating units M1 selected from the group consisting of a polymerized C 1 -C 10 -alkyl (meth)acrylate, a polymerized C 1 -C 10 -alkyl-(poly-C 2 -C 4 -alkyleneglycol) (meth)acrylate and a polymerized vinylaromatic hydrocarbon compound.

2. The polymer P of 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;
X is selected from the group consisting of linear C 2 -C 6 alkylene, C 2 -alkenylene and 1,2-phenylene, where C 2 -C 6 alkylene and C 2 -alkenylene are unsubstituted or carry a C 1 -C 18 alkyl or C 1 -C 18 alkenyl radical and 1,2-phenylene is unsubstituted or substituted by 1 or 2 radicals selected from the group consisting of C 1 -C 3 alkyl, —COOH or halogen;
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; and
Y is selected from —OH.

3. The polymer P of claim 2 , wherein:
k and m are both 0;
R 2 is hydrogen; and
X is C 2 -C 4 alkylene.

4. The polymer P of claim 1 , which is a poly-(C 2 -C 4 -alkylene oxide).

5. The polymer P of claim 1 , which is an aliphatic polyester.

6. The polymer P of claim 1 , which is an aliphatic polyether-ester.

7. The polymer P of claim 1 , which is an aliphatic polycarbonate.

8. The polymer P of claim 1 , which has a C—C-backbone comprising repeating units M1 selected from a polymerized C 1 -C 10 -alkyl (meth)acrylate, a polymerized C 1 -C 10 -alkyl-(poly-C 2 -C 4 -alkyleneglycol) (meth)acrylate and a polymerized vinylaromatic hydrocarbon compound, wherein the repeating units M1 make up from 10 to 90% by weight of the polymer P.

9. The polymer P of claim 1 , which has a number average weight in the range from 500 to 100,000 Dalton.

10. The polymer P of claim 1 , which has an acid number in the range of from 3 to 500 mg KOH/g.

11. A process for manufacturing the polymer P of claim 1 , the process comprising reacting
a polymer P.1 comprising at least one radical of formula (I.1):

bound to one of the termini and/or backbone of the polymer; and
reacting the polymer P.1 with an acid anhydride of formula (IV):

wherein X′ is a divalent moiety selected from the group consisting of linear C 1 -C 10 alkylene, linear C 2 -C 6 alkenylene, C 4 -C 7 cycloalkylene, arylene and alkarylene, where the linear C 1 -C 10 alkylene, linear C 2 -C 6 alkenylene and C 4 -C 7 cycloalkylene are unsubstituted or substituted by 1, 2, 3 or 4 radicals selected from the group consisting of C 1 -C 18 alkyl or C 1 -C 18 alkenyl, and where arylene and alkarylene 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 haloalkyl, aryl, —COOH, —COOCH 3 , —NO 2 or halogen, such that if X′ carries 2, 3 or 4 COOH groups, two COOH groups optionally form an anhydride group.

12. The process of claim 11 , comprising reacting a polymer P′ comprising 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):

wherein:
R L is hydrogen or a hydrocarbon radical having 1 to 8 carbon atoms; and
the polymer P′ does not have a functional group of the formula (I.1

Assignees

• Basf Se

Inventors

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

Classifications

• C08J7/0427

  with only one layer of a composition containing a polymer binder (with more layers C08J7/042) · CPC title

• C08F2438/02

  Stable Free Radical Polymerisation [SFRP]; Nitroxide Mediated Polymerisation [NMP] for, e.g. using 2,2,6,6-tetramethylpiperidine-1-oxyl [TEMPO] · CPC title

• C08G64/42

  Chemical after-treatment · CPC title

• C08J2400/10

  Polymers characterised by the presence of specified groups, e.g. terminal or pendant functional groups · CPC title

• C08G63/91

  Polymers modified by chemical after-treatment · CPC title