Polyamine addition compounds

• US 10,640,611 B2
• Filed: 11/28/2014
• Issued: 05/05/2020
• Est. Priority Date: 11/29/2013
• Status: Active Grant

• Current Assignee: BYK-Chemie GmbH (Susanne Klatten, MBA)
• Original Assignee: BYK-Chemie GmbH (Susanne Klatten, MBA)
• Inventors: Gobelt, Bernd, Okkel, Andreas, Omeis, Jurgen, Pritschins, Wolfgang, Bomer, Jorg, Stelz, Sabine, Esser, Andrea
• Primary Examiner(s): Uselding, John E
• Application Number:
  US15/038,379
• Publication Number:
  US 20170190840A1
• Time in Patent Office: 1,985 Days
• CPC Class Codes: C08G 63/6852 derived from hydroxy carboxylic acids
• CPC Class Codes: C08G 63/912 derived from hydroxycarboxylic acids
• CPC Class Codes: C08G 73/0206 Polyalkylene(poly)amines

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.

Claims

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)

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 NH₃ 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—

R¹NCO 

 

(II)

in which R¹ 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)

8. The method as claimed in claim 1, characterized in that component S comprises an acrylate of the general formula (IV)

H₂C═

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(X¹)_r 

 

(V)

(OH)_3-vPO(O—

Y(X¹)_r)_v 

 

(VI)

Y—

SO₂—

OH 

 

(VII)

in which X¹=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 greater color strength relative to untreated solid thus used.

17. The method as claimed in claim 1, whereby the dispersion, carrier medium or suspension into which the amino group-comprising polymer PAS or salt thereof is introduced or added exhibits lower surface tension or interfacial tension, and increased wetting capacity relative to the dispersion, carrier medium or suspension without the amino group-comprising polymer PAS or salt thereof.