# US 4,393,179 A · Synthetic resin

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- Number: US 4,393,179 A
- Document ID: US4393179A
- Status: Granted
- Kind: A
- Application number: 06/324,109
- Filed: 1981-11-23
- Granted: 1983-07-12
- Earliest claimed: 1980-12-01
- Assignees: BASF Farben & Fasern AG
- Inventors: Karl Hoppe; Udo Strauss
- Web page: https://patentgrep.com/patent/US4393179A

## CPC

- C08G 59/623: {Aminophenols}
- C08G 18/0814: {containing ammonium groups or groups forming them}
- C09D 5/4419: {with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds}
- C09D 5/4465: {Polyurethanes}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)

## Abstract

A synthetic resin is in the form of a metal complex compound. The resin is the reaction product of: (a) Mannich bases which are free from epoxide groups; with (b) epoxide resins; wherein aliphatic hydroxyl groups originating from (a), (b), or a mixture thereof, are at least partially converted into urethane groups by reaction with partially blocked isocyanate, said Mannich bases (a) formed from components selected from: (a.sub.1) condensed phenols which are free from ether groups and contain at least two aromatic rings and at least two phenolic hydroxyl groups; (a.sub.2) condensed phenols which contain ether groups and contain at least two aromatic rings and at least two phenolic hydroxyl groups; (a.sub.5) formaldehyde or compounds which split off formaldehyde; (a.sub.3) secondary amines having at least one hydroxyalkyl group; and (a.sub.4) dialkylamines or dialkoxyalkylamines which do not contain free hydroxyl groups; or from the components: (a.sub.1) and (a.sub.2) with (a.sub.5) and (a.sub.3); (a.sub.1) with (a.sub.5) and (a.sub.3); (a.sub.2) with (a.sub.5) and (a.sub.3); (a.sub.1) with (a.sub.5), (a.sub.3), and (a.sub.4); or (a.sub.2) with (a.sub.5), (a.sub.3), and (a.sub.4); and copper bound with the reaction product to form the metal complex compound.

## Claims

### Claim 1

A synthetic resin in the form of a metal complex compound comprising a reaction product of:
(a) Mannich bases which are free from epoxide groups; with
(b) epoxide resins; wherein aliphatic hydroxy groups originating from (a), (b), or a mixture thereof are at least partially converted into urethane groups by reaction with partially blocked isocyanate, said Mannich base (a) formed from components selected from:
(a.sub.1) condensed phenols which are free from ether groups and contain at least two aromatic rings and at least two phenolic hydroxyl groups;
(a.sub.2) condensed phenols which contain other groups and contain at least two aromatic rings and at least two phenolic hydroxyl groups;
(a.sub.5) formaldehyde or compounds which split off formaldehyde;
(a.sub.3) secondary amines having at least two hydroxyalkyl group; and
(a.sub.4) dialkylamines or dialkoxyalkylamines which do not contain free hydroxyl groups; or from the components:
(a.sub.1) and (a.sub.2) with (a.sub.5) and (a.sub.3);
(a.sub.1) with (a.sub.5) and (a.sub.3);
(a.sub.2) with (a.sub.5) and (a.sub.3);
(a.sub.1) with (a.sub.5), (a.sub.3), and (a.sub.4); or
(a.sub.2) with (a.sub.5), (a.sub.3), and (a.sub.4); and copper complex bound with said reaction product to form said metal complex compound.

### Claim 2 (depends on 1)

The synthetic resin of claim 1, wherein 0.5 to 0.6 part by weight of said copper are bonded to each 1,000 parts by weight of said reaction product.

### Claim 3 (depends on 2)

The synthetic resin of claim 2, wherein said reaction product is protonated by acids.

### Claim 4 (depends on 1)

The synthetic resin of claim 1 having an absorption band between 350 and 500 nm.

### Claim 5 (depends on 1)

A process for the preparation of the synthetic resin in accordance with claim 1, which comprises reacting a copper salt solution with a solution of said reaction product.

### Claim 6 (depends on 3)

Stoved coatings on the surface of electrically conductive substrates prepared by connecting said substrates as the cathode in a coating bath comprising said metal complex compound of claim 3, carrying out a cathodic electrocoating lacquering process and stoving the electrodeposited coatings resulting therefrom.

### Claim 7 (depends on 1)

The synthetic resin of claim 1, wherein said Mannich bases are formed from components (a.sub.1) with (a.sub.5) and (a.sub.3).

### Claim 8 (depends on 1)

The synthetic resin of claim 1, wherein said Mannich bases are formed from components (a.sub.2) with (a.sub.5) and (a.sub.3).

### Claim 9 (depends on 1)

The synthetic resin of claim 1, wherein said Mannich bases are formed from components (a.sub.1) and (a.sub.2) with (a.sub.5) and (a.sub.3).

### Claim 10 (depends on 1)

The synthetic resin of claim 1, wherein said Mannich bases are formed from components (a.sub.1) and (a.sub.2) with (a.sub.5), (a.sub.3), and (a.sub.4).

### Claim 11 (depends on 1)

The synthetic resin of claim 1, wherein said Mannich bases are formed from components (a.sub.1) with (a.sub.5), (a.sub.3), and (a.sub.4).

### Claim 12 (depends on 1)

The synthetic resin of claim 1, wherein said Mannich bases are formed from components (a.sub.2) with (a.sub.5), (a.sub.3), and (a.sub.4).

### Claim 13 (depends on 1)

The synthetic resin of claim 1, wherein said copper complex is bound with a salt selected from the group consisting of copper (II) acetate, copper (II) sulfate, and copper (II) nitrate.

### Claim 14 (depends on 13)

The synthetic resin of claim 13, wherein said metal complex compound is formed by reacting component (a) with component (b) in the presence of said copper salt.

### Claim 15 (depends on 13)

The synthetic resin of claim 13, wherein said metal complex compound is formed by reacting the reaction product of components (a) and (b) with said copper salt.

### Claim 16

A synthetic resin in the form of a metal complex compound which is substantially free from epoxide groups and is obtained by reacting
(a) mannich bases of
(a.sub.1) at least one condensed phenol which is free from ether groups and contains at least two aromatic rings and at least two phenolic hydroxyl groups per molecule,
(a.sub.2) at least one condensed phenol containing at least one ether group per molecule and also at least two aromatic rings and at least one phenolic hydroxyl group per molecule,
(a.sub.3) at least one secondary amine containing at least one hydroxyalkyl group or a mixture of one such secondary amine with at least one secondary dialkyl amine or dialkoxyalkyl amine which do not contain free hydroxyl groups,
(a.sub.4) formaldehyde or a formaldehyde-forming compound, with
(b) at least one epoxide resin
in which reaction product copper being complex-bonded by reacting component (a) with component (b) in the presence of a copper salt or by reacting the reaction product of (a) and (b) with said copper salt, the copper complex compound having 0.5 to 0.6 part by weight of copper bonded to each 1,000 parts by weight of the reaction product of (a) and (b).

### Claim 17 (depends on 16)

The synthetic resin of claim 16, wherein the reaction product of (a) and (b) contains urethane groups, which have been obtained by reacting a partially blocked isocyanate with the mannich bases (a) or the epoxide resins (b) or the reaction product of (a) and (b).

### Claim 18 (depends on 16)

The synthetic resin of claim 16, obtained by reacting mannich bases (a) which have been obtained from a.sub.1 or a.sub.2 with a.sub.3 and a.sub.4.

### Claim 19 (depends on 1)

The synthetic resin of claim 1, obtained by reacting mannich bases (a) which have been obtained under the following conditions:
the ratio of components a.sub.1 to a.sub.2 is from 1:0.1 to 1:5 by weight; the ratio of components a.sub.3 to a.sub.4 is from 1:10 to 1:0.1 by weight; the ratio of moles a.sub.1 +a.sub.2 to a.sub.3 +a.sub.4 is from 1:0.75 to 1:3 by weight and at least one mole of component a.sub.5 is used for one mole of a.sub.3 +a.sub.4.

### Claim 20 (depends on 16)

The synthetic resin of claim 16, wherein from 50 to 90 percent by weight of component (a) is reacted with from 10 to 50 percent by weight of component (b).

### Claim 21 (depends on 16)

The synthetic resin of claim 16, protonized with inorganic acids or water-soluble organic acids or mixtures thereof.