Amine adducts preparable by Michael addition

Patent metadata

Field	Value
Publication number	US-9752067-B2
Application number	US-201214358508-A
Country	US
Kind code	B2
Filing date	Nov 15, 2012
Priority date	Nov 18, 2011
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

The invention relates to a process for preparing an amine adduct, in which a polyamine component (A), a polyester component (B) and a hydrocarbon component (C) are reacted. The amine adduct is of particularly good suitability as a wetting agent and dispersant, especially for coatings and plastics applications.

First claim

The invention claimed is:

1. A process for preparing an amine adduct, in which a polyamine component (A), a polyester component (B) and a hydrocarbon component (C) are reacted in weight ratios of
(A):(B)=1:1000 to 1:1 and
(A):(C)=1:100 to 100:1
in that according to reaction variant i) first a reaction intermediate (A-B) is produced from the polyamine component (A) and the polyester component (B), which is subsequently reacted with the hydrocarbon component (C) or
according to reaction variant ii) first a reaction intermediate (A-C) is formed from the polyamine component (A) and the hydrocarbon component (C) and this is subsequently reacted with the polyester component (B) or
according to reaction variant iii) the polyamine component (A) is reacted simultaneously with the polyester component (B) and the hydrocarbon component (C)
wherein the polyester component (B) and the hydrocarbon component (C) do not react with one another under the reaction conditions of the reaction,
the polyamine component (A) is present in the form of at least one organic polyamine compound (A′), which in each case has at least three amino groups (A′+) selected from primary and secondary amino groups, in each case reactive with both the polyester component (B) and the hydrocarbon component (C),
the polyester component (B) is present in the form of at least one polyester compound (B′), which in each case contains no primary amino groups and no secondary amino groups, in each case has at least three ester groups, and in each case contains a coupling group (B′+) present as a carboxyl group or carboxylic acid anhydride group, reactive with primary and/or secondary amino groups, and
the hydrocarbon component (C) is present in the form of at least one branched or unbranched, saturated or unsaturated hydrocarbon compound (C′) each having a linking group (C′+), in each case (C′) having no primary amino groups, in each case having no secondary amino groups, in each case having no carboxyl groups with the exception of a COOH substituent as an alternative moiety of the linking group (C′+), and in each case having no carboxylic acid anhydride groups, and in each case (C′) having an overall ratio of carbon atoms to hetero atoms of at least 2:1, wherein the hetero atoms are selected from the group of elements consisting of at least one of elements O, N, P, S, and Si, wherein the linking group (C′+) in each case has the characteristic of reacting with primary amino groups with formation of secondary amino groups and/or with secondary amino groups with formation of tertiary amino groups, and also in each case is present in the form of an activated alkenyl function of formula (I)
R 4 R 5 C═CR 6 R 7   (I)

with R 4 , R 5 , R 6 and R 7 in each case independently from one another represented by an electron-withdrawing substituent E, by H or by a saturated or unsaturated, branched or unbranched C 1 -C 12 hydrocarbon moiety, with the specification that a total of two of the moieties from the group R 4 , R 5 , R 6 and R 7 may be joined together by ring closure, that at least one of the moieties from the group R 4 , R 5 , R 6 and R 7 is present as an electron-withdrawing substituent, and that one of the moieties from the group R 4 , R 5 , R 6 and R 7 is a bivalent unit over which the linking group (C′+) is connected to the other part of the hydrocarbon compound (C′),
wherein the electron-withdrawing substituent E in each case is the same or different and is represented by COR E , COOR E , CONHR E , CONR E 2 , or CN and the moieties R E in each case are the same or different and independently of one another are represented by H or an aliphatic, aromatic or aliphatic-aromatic moiety.

2. The process according to claim 1 , wherein the reaction of (A), (B) and (C) is performed in weight ratios of
(A):(B)=1:100 to 1:4 and
(A):(C)=1:10 to 10:1.

3. The process according to claim 1 , wherein at least 50% by weight of the polyester compounds (B′) used are present in the form of linear, monocarboxy-functional caprolactone polyesters.

4. The process according to claim 3 , wherein the at least 50% by weight of the polyester compounds (B′) used are present in the form of linear, monocarboxy-functional caprolactone polyesters, which each has a weight-average molecular weight of 500 to 10,000.

5. The process according to claim 1 , wherein the hydrocarbon component (C) contains at least 30% by weight of unsaturated C 6 -C 50 hydrocarbon compounds (C′), which in each case contains at least one alkyl and/or alkylaryl moiety.

6. The process according to claim 1 , wherein the hydrocarbon component (C) contains at least 30% by weight of unsaturated C 10 -C 70 hydrocarbon compounds (C′), which in each case contains at least one branched alkyl and/or one branched alkenyl moiety.

7. The process according to claim 1 , wherein components (A), (B) and (C) are used respectively in stoichiometric ratios such that altogether at least 50 mol % of the totality of the reactive amino groups (A′+) of the polyamine compounds (A′) used are reacted with the polyester compounds (B′) and/or with the hydrocarbon compounds (C′).

8. The process according to claim 1 , wherein the reaction of (A), (B) and (C) is performed in weight ratios of
(A):(B)=1:25 to 1:7 and
(A):(C)=1:2 to 2:1.

9. The process according to claim 1 , wherein 70 to 100% by weight of the polyester compounds (B′) used are present in the form of linear, monocarboxy-functional caprolactone polyesters.

10. The process according to claim 9 , wherein the 70 to 100% by weight of the polyester compounds (B′) used are present in the form of linear, monocarboxy-functional caprolactone polyesters, which each has a weight-average molecular weight of 500 to 10,000.

11. The process according to claim 1 , wherein the hydrocarbon component (C) contains 50 to 100% by weight of unsaturated C 6 -C 50 hydrocarbon compounds (C′), which in each case contains at least one alkyl and/or alkylaryl moiety.

12. The process according to claim 1 , wherein the hydrocarbon component (C) contains 50 to 100% by weight of unsaturated C 10 -C 70 hydrocarbon compounds (C′), which in each case contains at least one branched alkyl and/or one branched alkenyl moiety.

13. The process according to claim 1 , wherein components (A), (B) and (C) are used respectively in stoichiometric ratios such that altogether 70 to 100 mol % of the totality of the reactive amino groups (A′+) of the polyamine compounds (A′) used are reacted with the polyester compounds (B′) and/or with the hydrocarbon compounds (C′).

Assignees

• Byk Chemie Gmbh

Inventors

• Pritschins Wolfgang
• Omeis Jürgen
• Mössmer Stefan
• Esser Andrea
• Roch Monika

Classifications

• C08G63/914

  derived from polycarboxylic acids and polyhydroxy compounds · CPC title

• C08L67/04

  Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C08L67/06 takes precedence) · CPC title

• C08G63/912

  derived from hydroxycarboxylic acids · CPC title

• C09D17/00

  Pigment pastes, e.g. for mixing in paints (artists' paints C09D5/06) · CPC title

• C08G63/6854

  derived from polycarboxylic acids and polyhydroxy compounds · CPC title