Monomers and polymers

Patent metadata

Field	Value
Publication number	US-11053334-B2
Application number	US-201716343594-A
Country	US
Kind code	B2
Filing date	Oct 24, 2017
Priority date	Nov 4, 2016
Publication date	Jul 6, 2021
Grant date	Jul 6, 2021

Abstract

The presently claimed invention relates to novel monomers which can be used for preparing polymers which are useful as dispersants for pigments and fillers, as wetting agent and as thickening agents in liquid compositions.

First claim

The invention claimed is:

1. A compound of formula (I)

where
each R is independently halogen, OH, NO 2 , C 1 -C 4 -alkyl, C 1 C 4 -alkoxy, CONH 2 , NH—CHO, NH—C 1 C 4 -alkyl, or NH—(C═O)—C 1 -C 4 -alkyl;
k is 0, 1, 2, 3 or 4;
R 1 is hydrogen or C 1 -C 4 -alkyl;
R 2 is hydrogen or C 1 -C 40 -hydrocarbyl;
each R 3 is independently hydrogen or C 1 -C 2 -alkyl;
a is from 0 to 1500;
b is from 0 to 1500; and
c is from 0 to 750,
wherein a+b+c is from 2 to 1500; and
the “a” repeating units [—O—CH 2 —CH(R 3 )—], the “b” repeating units [—O—CH(R 3 )—CH 2 —] and the “c” repeating units [—O—CH 2 CH 2 CH 2 CH 2 —] are distributed statistically or form a gradient or a block structure.

2. The compound of formula (I) according to claim 1 , wherein c is 0.

3. The compound of formula (I) according to claim 1 , wherein R 2 is C 1 -C 40 -hydrocarbyl.

4. The compound of formula (I) according to claim 1 , wherein a+b+c is from 2 to 500.

5. The compound of formula (I) according to claim 1 , wherein k is 0.

6. The compound of formula (I) according to claim 1 , wherein R 1 is hydrogen or methyl.

7. The compound of formula (I) according to claim 1 , wherein R 3 is hydrogen or methyl.

8. A method for preparing the compound of formula (I) according to claim 1 , the method comprising
i) reacting a polyalkyleneoxide of formula (II-H)

where R 2 , R 3 , a, b and c are as defined in claim 1 ;
with an unsubstituted or substituted isatoic anhydride or an ester forming derivative of unsubstituted or substituted anthranilic acid to obtain a product, wherein the substituted isatoic anhydride and substituted anthranilic acid are substituted with k substituents R on the phenyl ring, wherein R and k are as defined in claim 1 ; and
ii) reacting the product obtained in i) with a compound of formula (III)
CH 2 ═C(R 1 )—C(O)—X   (III)

where R 1 is as defined in claim 1 and X is halogen, C 1 -C 4 -alkoxy or CH 2 ═C(R 1 )—C(O)—.

9. The method according to claim 8 , wherein the compound of formula (III) is acrylic anhydride or methacrylic anhydride.

10. A polymer having a C—C-backbone, comprising repeating units of formula (IV),

where R, R 1 , R 2 , R 3 , a, b, c and k are as defined in claim 1 ,
wherein
the “a” repeating units [—O—CH 2 —CH(R 3 )—], the “b” repeating units [—O—CH(R 3 )—CH 2 —] and the “c” repeating units [—O—CH 2 CH 2 CH 2 CH 2 —] are distributed statistically or form a gradient or a block structure.

11. A polymer, obtained by a process comprising: polymerizing monomers M, comprising at least one monomer of formula (1) as defined in claim 1 .

12. The polymer according to claim 11 , wherein the monomers M further comprise at least one monomer M2, which is an ethylenically unsaturated compound different from the compound of formula (I).

13. The polymer according to claim 12 , wherein the monomer M2 is selected from the group consisting of a vinylaromatic hydrocarbon, a monoethylenically unsaturated carboxylic acid, a primary amide of a monoethylenically unsaturated carboxylic acid, an N-mono-C 1 -C 20 -alkyl amide of a monoethylenically unsaturated carboxylic acid, an N,N-di-C 1 -C 20 -alkyl amide of a monoethylenically unsaturated carboxylic acid, a C 1 -C 20 -alkyl ester of a monoethylenically unsaturated carboxylic acid, a C 3 -C 10 -cycloalkyl ester of a monoethylenically unsaturated carboxylic acid, a (di-C 1 -C 20 -alkylamino-C 2 -C 4 -alkyl) ester of a monoethylenically unsaturated carboxylic acid, a (tri-C 1 -C 20 -alkylammonium-C 2 -C 4 -alkyl) ester of a monoethylenically unsaturated carboxylic acids acid, an N (tri-C 1 -C 20 -alkylammonium-C 2 -C 4 -alkyl) amide of a monoethylenically unsaturated carboxylic acid, an N-(di-C 1 -C 20 -alkylamino-C 2 -C 4 -alkyl) amide of a monoethylenically unsaturated carboxylic acid, a vinyl substituted heterocycle, and a morpholide of a monoethylenically unsaturated carboxylic acid.

14. The polymer according to claim 13 , wherein the monomer M2 is selected from the group consisting of styrene, acrylic acid, methacrylic acid, fumaric acid, itaconic acid, maleic acid, 2-(N,N-dimethylamino)ethyl methacrylate, (2-(methacryloyloxy)-ethyl)trimethyl ammonium chloride, 1-vinylimidazole, dimethylacrylamide, and N-acryloylmorpholine.

15. The polymer according to claim 11 , wherein the monomer of formula (I) makes up from 1 mol-% to 99 mol-% of monomers M.

16. A method for preparing the polymer according to claim 11 , the method comprising: polymerizing monomers M via a free radical polymerization.

17. A liquid composition, comprising at least one polymer according to claim 10 , which is in a form of a liquid dispersion.

18. The liquid composition according to claim 17 , further comprising a fine particulate solid material, which is a pigment or a filler.

Assignees

• Basf Se

Inventors

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

Classifications

• C09D133/24 Primary

  Homopolymers or copolymers of amides or imides · CPC title

• C08F220/58 Primary

  containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine} · CPC title

• C09D5/027

  Dispersing agents (anti-settling agents C09D7/45) · CPC title

• C08F220/585

  and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS] · CPC title

• C08F220/06

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title