POLYAMINE ADDITION COMPOUNDS

• US 20170190840A1
• Filed: 11/28/2014
• Published: 07/06/2017
• 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: GBELT, Bernd, OKKEL, Andreas, OMEIS, Jrgen, PRITSCHINS, Wolfgang, BMER, Jrg, STELZ, Sabine, EER, Andrea
• Granted Patent: US 10,640,611 B2
• Time in Patent Office: 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 wetting agents and dispersing agents, and paints and plastic materials containing said addition compounds.

Claims

1. An amino group-comprising polymer PAS or salt thereof obtainable by reaction with an acid, the polymer being obtainable 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) l=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 polymer PAS as claimed in claim 1, characterized in that the intermediate PA is preparable 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 polymer PAS 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 polymer PAS as claimed in claim 1, characterized in that the intermediate PA is a dendritic polyamine which is preparable 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 polymer PAS as claimed in claim 1, characterized in that the intermediate PA is preparable by reaction of an amine A with compounds P which comprise two to six epoxide groups and/or acrylic groups.

6. The polymer PAS as claimed in claims 1-5, 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 polymer PAS as claimed in claims 1-5, characterized in that component S comprises a uretdione compound of the general formula (III)

8. The polymer PAS as claimed in claims 1-5, 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 polymer PAS as claimed in claims 1-5, 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 obtainable 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 polymer PAS as claimed in claims 1-5, characterized in that it is obtainable 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.

21. The use of the amino group-comprising polymer PAS as claimed in claim 1 to 10 as wetting agent and/or dispersant.

22. A coating material comprising an amino group-comprising polymer PAS as claimed in claim 1 to 10.

23. A plastic comprising an amino group-comprising polymer PAS as claimed in claim 1 to 10.

11. A process for preparing an amino group-comprising polymer PAS by a multistage synthesis wherein an intermediate PA is prepared by reaction of at least one compound P with at least one 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) l=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)

12. The process as claimed in claim 11, 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.

13. The process as claimed in claim 12, characterized in that the further groups that are reactive toward the ester are primary or secondary amino groups and/or hydroxyl groups.

14. The process as claimed in claim 11, characterized in that a dendritic polyamine as intermediate PA is prepared by reaction in a first stage of ammonia or an amine A and an alkyl acrylate as component P with one another and in at least one further stage the resulting reaction product is reacted with a stoichiometric excess of diamine.

15. The process as claimed in claim 11, 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.

16. The process as claimed in claims 11-15, 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.

17. The process as claimed in claims 11-16, characterized in that component S comprises a uretdione compound of the general formula (III)

18. The process as claimed in claims 11-17, characterized in that component S is 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.

19. The process as claimed in claims 11-18, characterized in that the intermediate PA, or a PA modified by reaction of PA by one or more of the reactions as per (a), (b) and (c), is reacted 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.

20. The process as claimed in claims 11-19, characterized in that the intermediate PA, or a PA modified by reaction of PA by one or more of the reactions (a), (b), and (c), is reacted with at least one lactone or with a mixture of lactones in a ring-opening polymerization.