# US 9,752,067 B2 · Amine adducts preparable by Michael addition

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- Number: US 9,752,067 B2
- Document ID: US9752067B2
- Status: Granted
- Kind: B2
- Application number: 14/358,508
- Filed: 2012-11-15
- Published: 2014-10-02
- Granted: 2017-09-05
- Earliest claimed: 2011-11-18
- Assignees: BYK-Chemie GmbH
- Applicants: Byk-Chemie GmbH
- Inventors: Wolfgang Pritschins; Jürgen Omeis; Stefan Mössmer; Andrea Esser; Monika Roch
- Web page: https://patentgrep.com/patent/US9752067B2

## CPC

- C09D 7/45: Anti-settling agents
- C08G 63/685: containing nitrogen
- C08G 63/6854: {derived from polycarboxylic acids and polyhydroxy compounds}
- C08G 63/912: {derived from hydroxycarboxylic acids}
- C08G 63/914: {derived from polycarboxylic acids and polyhydroxy compounds}
- C09D 11/30: Inkjet printing inks
- C09D 17/00: Pigment pastes, e.g. for mixing in paints (artists' paints C09D5/06)
- C09D 167/04: Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C09D167/06 takes precedence)
- C09J 167/04: Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C09J167/06 takes precedence)
- C08L 67/00: Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain (of polyester-amides C08L77/12; of polyester-imides C08L79/08); Compositions of derivatives of such polymers
- C08L 67/04: Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C08L67/06 takes precedence)
- C08L 2666/34: Oxygen-containing compounds, including ammonium and metal salts
- C08L 2666/36: Nitrogen-containing compounds
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## 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.

## Claims

### Claim 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)
R4R5C═CR6R7 (I)
with R4, R5, R6 and R7 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 C1-C12 hydrocarbon moiety, with the specification that a total of two of the moieties from the group R4, R5, R6 and R7 may be joined together by ring closure, that at least one of the moieties from the group R4, R5, R6 and R7 is present as an electron-withdrawing substituent, and that one of the moieties from the group R4, R5, R6 and R7 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 CORE, COORE, CONHRE, CONRE2, or CN and the moieties RE 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.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

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.

### Claim 4 (depends on 3)

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.

### Claim 5 (depends on 1)

The process according to claim 1, wherein the hydrocarbon component (C) contains at least 30% by weight of unsaturated C6-C50 hydrocarbon compounds (C′), which in each case contains at least one alkyl and/or alkylaryl moiety.

### Claim 6 (depends on 1)

The process according to claim 1, wherein the hydrocarbon component (C) contains at least 30% by weight of unsaturated C10-C70 hydrocarbon compounds (C′), which in each case contains at least one branched alkyl and/or one branched alkenyl moiety.

### Claim 7 (depends on 1)

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′).

### Claim 8 (depends on 1)

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.

### Claim 9 (depends on 1)

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.

### Claim 10 (depends on 9)

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.

### Claim 11 (depends on 1)

The process according to claim 1, wherein the hydrocarbon component (C) contains 50 to 100% by weight of unsaturated C6-C50 hydrocarbon compounds (C′), which in each case contains at least one alkyl and/or alkylaryl moiety.

### Claim 12 (depends on 1)

The process according to claim 1, wherein the hydrocarbon component (C) contains 50 to 100% by weight of unsaturated C10-C70 hydrocarbon compounds (C′), which in each case contains at least one branched alkyl and/or one branched alkenyl moiety.

### Claim 13 (depends on 1)

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′).