Polyamine addition compounds

Patent metadata

Field	Value
Publication number	US-10640611-B2
Application number	US-201415038379-A
Country	US
Kind code	B2
Filing date	Nov 28, 2014
Priority date	Nov 29, 2013
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

The invention relates to polyamine addition compounds, methods for the production thereof, the use thereof as crosslinking agents and dispersing agents, and paints and plastic materials containing the addition compounds.

First claim

The invention claimed is:

1. A method comprising utilizing an amino group-comprising polymer PAS or salt thereof as wetting agent and/or dispersant, the amino group-comprising polymer PAS or salt thereof obtained by reaction with an acid, the polymer being obtained by a multistage synthesis wherein an intermediate PA is prepared by reaction of at least one compound P with at least an amine A, the compound P comprising 2 to 6 groups that are reactive toward hydroxyl groups and/or amino groups, and the amine A comprising
(i) m=1 to 8 primary and/or secondary amino groups,
(ii) n=0 to 5 hydroxyl groups and
(iii) 1=0 to 5 tertiary amino groups, where
(iv) m+n≥2 and
(v) the compound A besides nitrogen atoms, oxygen atoms, and hydroxyl groups contains only hydrocarbon groups, and

the intermediate PA has structural units of the general formula (I)

in which
X 1 =H or OH,
X 2 =CH 2 or C═O, and
X 3 =O or NH,
and where the intermediate PA
(a) is reacted with one or more components S that are reactive toward hydroxyl groups and/or amino groups, to give an amino group-comprising polymer, and/or
(b) is reacted in a ring-opening polymerization with at least one lactone or with a mixture of lactones, to give an amino group-comprising polymer,
(c) and 0-80% of the primary and secondary amino groups present originally in the intermediate PA are reacted with one or more species of a component U, selected from the group of the hydroxyl-functional acrylates and/or a cyclic compound selected from the group of the oxiranes and oxetanes, the lactones, and cyclic carbonates, the reaction taking place with introduction of hydroxyl groups,
whereby the reactions under (a), (b), and (c) may take place in any desired combination and temporal sequence relative to one another;
wherein said utilizing as a wetting agent and/or dispersant comprises dispersing solid therein; admixing with, applying to, or coating on a solid; introducing in or adding to a dispersion containing solid or a suspension including solid; wherein said solid is a pigment or filler, wherein the amino group-comprising polymer PAS or salt thereof functions as a wetting agent and/or dispersant for the pigment or filler;
or wherein said utilizing as a wetting agent and/or dispersant comprises adding amino group-comprising polymer PAS or salt thereof to a carrier medium and adding solid thereto; wherein said solid is a pigment or filler, and wherein the amino group-comprising polymer PAS or salt thereof functions as a wetting agent and/or dispersant for the pigment or filler.

2. The method as claimed in claim 1 , characterized in that the intermediate PA is prepared by reaction of ethylenically unsaturated ester compounds P, in which the C═C double bond and the carbonyl double bond of the ester are conjugated, with diamines or with amines which as well as a primary amino group comprise at least one further group that is reactive toward the ester, or which as well as a secondary amino group comprise at least two further groups that are reactive toward the ester.

3. The method as claimed in claim 2 , characterized in that the further groups that are reactive toward the ester are primary or secondary amino groups and/or hydroxyl groups.

4. The method as claimed in claim 1 , characterized in that the intermediate PA is a dendritic polyamine which is prepared in a multistage reaction wherein in the first stage an amine A or NH 3 and an alkyl acrylate as component P are reacted with one another and in at least one further stage the reaction product is reacted with a stoichiometric excess of diamine.

5. The method as claimed in claim 1 , characterized in that the intermediate PA is prepared by reaction of an amine A with compounds P which comprise two to six epoxide groups and/or acrylic groups.

6. The method as claimed in claim 1 , characterized in that component S comprises an isocyanate adduct of the general formula (II)
Y—O—CO—NH—R 1 NCO  (II)

in which R 1 is alike or different and is represented by a saturated or unsaturated, branched or unbranched organic radical comprising 6 to 20 carbon atoms, and Y is a monomeric or polymeric group which is not reactive toward isocyanates and which comprises one or more aliphatic, cycloaliphatic, araliphatic and/or aromatic groups, with Y possessing a number-average molar mass of less than 20,000 g/mol.

7. The method as claimed in claim 1 , characterized in that component S comprises a uretdione compound of the general formula (III)

in which R 1 is alike or different and is represented by a saturated or unsaturated, branched or unbranched organic radical comprising 6 to 20 carbon atoms, and Y is a monomeric or polymeric group which is not reactive toward isocyanates and which comprises one or more aliphatic, cycloaliphatic, araliphatic and/or aromatic groups, with Y possessing a number-average molar mass of less than 20,000 g/mol.

8. The method as claimed in claim 1 , characterized in that component S comprises an acrylate of the general formula (IV)
H 2 C═CH—COO—Y  (IV)

in which Y is a monomeric or polymeric group which is not reactive toward isocyanates and which comprises one or more aliphatic, cycloaliphatic, araliphatic and/or aromatic groups, with Y possessing a number-average molar mass of less than 20,000 g/mol.

9. The method as claimed in claim 1 , characterized in that component S comprises an acid selected from the group of the carboxylic acids, phosphoric esters, and sulfonic acids, and the polymer PAS is obtained by reaction of the intermediate PA, or of a PA modified by reaction of PA by one or more of the reactions (a), (b) and (c), with compounds of the general formulae (V), (VI), or (VII)
(HOOC) p —Y(X 1 ) r   (V)

(OH) 3-v PO(O—Y(X 1 ) r ) v   (VI)

Y—SO 2 —OH  (VII)

in which X 1 =H or OH, p=1-3, r=1-5, v=1 or 2, and Y is a monomeric or polymeric group which is not reactive toward isocyanates and which comprises one or more aliphatic, cycloaliphatic, araliphatic and/or aromatic groups, with Y possessing a number-average molar mass of less than 20,000 g/mol.

10. The method as claimed in claim 1 , characterized in that the polymer PAS or salt thereof is obtained by reaction of the intermediate PA, or of a PA modified by reaction of PA by one or more of the reactions (a), (b), and (c) with at least one lactone or with a mixture of lactones in a ring-opening polymerization.

11. The method as claimed in claim 1 , characterized in that said solid is a pigment.

12. The method as claimed in claim 11 , wherein said method produces or processes a pigment concentrate containing the pigment solid.

13. The method as claimed in claim 1 , wherein said method produces or processes a filler solid.

14. The method as claimed in claim 1 , wherein said method produces or processes coating materials containing the pigment solid.

15. The method as claimed in claim 1 , wherein said method produces or processes a paint or varnish containing the pigment solid.

16. The method as claimed in claim 1 , whereby the pigment or filler solid which has been dispersed in, has been admixed with, has had applied thereto, or has been coated with the amino group-comprising polymer PAS or salt thereof, when used in a coating, paste or concentrate exhibits higher flocculation stability, increased gloss or

Assignees

• Byk Chemie Gmbh

Inventors

• Göbelt Bernd
• Okkel Andreas
• Omeis Jürgen
• Pritschins Wolfgang
• Bömer Jörg
• Stelz Sabine
• Esser Andrea

Classifications

• C08G63/6852 Primary

  derived from hydroxy carboxylic acids · CPC title

• C08G73/0206 Primary

  Polyalkylene(poly)amines · CPC title

• C09D167/00

  Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain (based on polyester-amides C09D177/12; based on polyester-imides C09D179/08); Coating compositions based on derivatives of such polymers · CPC title

• C08G63/912

  derived from hydroxycarboxylic acids · CPC title

• C09D11/102

  containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds · CPC title