KR-102963555-B1 - Comb-shaped polymer having base groups

KR102963555B1KR 102963555 B1KR102963555 B1KR 102963555B1KR-102963555-B1

Abstract

The present invention relates to a comb-shaped polymer having a polymer backbone and lateral side chains connected to the polymer backbone, wherein the lateral side chains comprise a) an alkyl ether-terminated polyalkylene oxide side chain and b) a tertiary amine-functional side chain, wherein the tertiary amine group is at least partially neutralized by an acid having a molecular weight in the range of 100 g/mol to 2000 g/mol, wherein the molecular weight relates to the number average molecular weight Mn for the polymeric acid, and wherein the lateral side chains a) and b) are distributed in a random order.

Inventors

요네하라, 히로시
린드너, 벤자민
오켈, 안드레아스
히노, 신지
스텔즈, 사비네
타카바야시, 료

Assignees

비와이케이-케미 게엠베하

Dates

Publication Date: 20260513
Application Date: 20220405
Priority Date: 20210407

Claims (15)

As a comb-shaped polymer having a polymer backbone and lateral side chains connected to the polymer backbone, Here, the polymer backbone comprises polymerized units of vinyl aromatic hydrocarbon monomers, and Here, the lateral side chain is a) alkyl ether-terminated polyalkylene oxide side chain, and b) tertiary amine-functional side chain It comprises, wherein the tertiary amine group is at least partially neutralized by an acid having a molecular weight in the range of 100 g/mol to 2000 g/mol, wherein in the case of a polymeric acid, the acid comprises a polyether segment or a polyester segment, and the molecular weight relates to the number average molecular weight Mn determined by gel permeation chromatography using a polystyrene standard for correction, and Here, lateral side chains a) and b) are distributed in a random order. Comb-shaped polymer.
A comb-shaped polymer according to claim 1, wherein the acid has a molecular weight in the range of 150 to 2000 g/mol, wherein the molecular weight is related to the number average molecular weight Mn in the case of a polymeric acid.
A comb-shaped polymer according to claim 1 or 2, wherein the acid comprises an acidic group including at least one of a carboxylic acid group, a phosphate group, and a sulfonic acid group.
A comb-shaped polymer according to claim 1 or 2, wherein at least 5 mol% of the tertiary amine groups are neutralized by an acid having a molecular weight in the range of 100 g/mol to 2000 g/mol, wherein, in the case of a polymeric acid, the acid comprises a polyether segment or a polyester segment, and the molecular weight relates to the number average molecular weight Mn determined by gel permeation chromatography using a polystyrene standard for correction.
A comb-shaped polymer according to claim 1 or 2, wherein the alkyl ether-terminated polyalkylene oxide side chains are connected to the polymer backbone through imide groups.
A comb-shaped polymer according to claim 1 or 2, wherein the amine-functional side chain is connected to the polymer backbone through an imide group.
A comb-shaped polymer according to claim 1 or 2, wherein the polymer backbone comprises polymerized units of N-substituted maleic imide.
A comb-shaped polymer according to claim 1 or 2, wherein the amine value of the polymer is in the range of 5 to 150 mg KOH/g.
(A) Comb-shaped polymer according to paragraph 1 or 2, (B) at least one coloring agent, and (C) At least one diluent A composition comprising
A composition according to claim 9, further comprising a membrane-forming binder (D).
A method of using a comb-shaped polymer according to claim 1 or 2 as a wetting agent, dispersant, or both a wetting agent and a dispersant for solid particles.
A method according to claim 11, wherein the solid particles comprise at least one of a pigment, a dye, and a filler.
A method for dispersing solid particles in a liquid dispersion medium, wherein a comb-shaped polymer according to claim 1 or 2 is present in the dispersion medium.
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Description

Comb-shaped polymer having base groups The present invention relates to a comb polymer having alkyl ether-terminated polyalkylene oxide side chains and neutralized tertiary amine-functional side chains, a composition comprising the comb polymer and at least one coloring agent, and the use of the comb polymer as a wetting agent and/or dispersant for solid particles. US 7078464 describes a composition comprising an unsaturated carboxylic acid salt of an amine-functionalized styrene-maleic anhydride copolymer. Its use as a pigment dispersant is also described. Preferred unsaturated carboxylic acids are acrylic acid and methacrylic acid. WO 2008/080580 describes a modified comb copolymer prepared by the reaction of an SMA resin with a polyalkylene oxide monoamine and a primary or tertiary diamine. The tertiary amine group is converted at least partially to a quaternary ammonium salt. The modified comb copolymer is suitable as a pigment dispersant resin. WO 2013/189568 describes copolymers and their uses as wetting agents and dispersants. Copolymers are prepared by reacting a main chain polymer with a primary amine or alcohol having at least one tertiary amine group, and then quaternizing it. In some embodiments, the main chain polymer may be modified with a polyalkylene oxide monoamine. The comb-shaped polymer of the present invention is suitable for use as a wetting agent and a dispersant and provides improved properties to aqueous and organic solvent-based pigment dispersions. The comb-shaped polymer results in the formation of pigment dispersions having low viscosity, excellent storage stability, and broad compatibility with various types of binders used in coating compositions and other colored compositions. When used in pigment dispersions for the manufacture of color resists for flat panel displays, improved development properties and excellent redissolvability are observed. The polymer is easily prepared from readily available raw materials without the need for sensitive polymerization techniques. The polymer of the present invention comprises a polymer backbone. The polymer backbone is a linear or branched polymer having repeating units. Preferably, the polymer backbone has a structure that is substantially or entirely linear. In general, the type of polymer forming the polymer backbone is not particularly limited and may be selected from polymer types known to those skilled in the art. Examples of suitable polymer types include polyesters, polyurethanes, polycarbonates, and polymers and copolymers of polymerizable ethylene-based unsaturated monomers. Given the wide variety of available ethylene-based unsaturated monomers having additional functional groups, polymers and copolymers of such monomers, collectively referred to as (co)polymers, are preferred as polymer backbones. Examples of suitable ethylene-based unsaturated monomers include vinyl esters, vinyl ethers, vinyl aromatic compounds such as styrene, acrylic acid, and methacrylic acid, as well as their esters and amides, collectively referred to as (meth)acrylates. Suitable monomers also include maleic acid and fumaric acid, as well as their derivatives, such as anhydrides, esters, amides, and imides. In a preferred embodiment, the polymer backbone comprises polymerized units of vinyl aromatic hydrocarbon monomers, particularly styrene. It is additionally preferable that the polymer backbone comprises polymerized units of N-substituted maleic imide. It is particularly preferable that lateral side chains a) and b) are connected to the polymer through the nitrogen atoms of the polymerized units of N-substituted maleic imide. In the polymer of the present invention, lateral side chains are connected to the polymer backbone. Generally, lateral side chains are connected to the polymer backbone by covalent bonds. The resulting structure may also be referred to as a comb polymer. Typically, two or more lateral side chains are covalently connected to the polymer backbone. The lateral side chain includes an alkyl ether-terminated polyalkylene oxide side chain. Alkyl ethers generally comprise an alkyl group having 1 to 32 carbon atoms. The alkyl group may be linear or branched. The alkyl group may likewise contain a cyclic group. In a preferred embodiment, the alkyl group has 1 to 8 carbon atoms. Polyalkylene oxide groups generally have a number average molecular weight in the range of 88 to 5000 g/mol. In a preferred embodiment, it is 132 to 4000 g/mol, more preferably 132 to 2000 g/mol. The number average molecular weight can be determined by gel permeation chromatography. The polyalkylene oxide group comprises polymerized units of alkylene oxide. The alkylene oxide is preferably selected from ethylene oxide, propylene oxide, and combinations thereof. It is particularly preferred that the polyalkylene oxide group comprises or consists of polymerized units of ethylene oxide. Where the polyalkylene oxide side chain comprises polymerized units of more than