Polyamine addition compounds

Patent metadata

Field	Value
Publication number	US-2017190840-A1
Application number	US-201415038379-A
Country	US
Kind code	A1
Filing date	Nov 28, 2014
Priority date	Nov 29, 2013
Publication date	Jul 6, 2017
Grant date	—

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.

First claim

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)

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.

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

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.

8 . The polymer PAS as claimed in claims 1 - 5 , 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 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(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 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.

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)

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.

12 . The process as claimed in claim 11 , characterized in that the inte

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

• C09D11/102

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

• C08G73/0206 Primary

  Polyalkylene(poly)amines · CPC title

• C08G63/912

  derived from hydroxycarboxylic acids · CPC title