# US 5,344,859 A · Water-dilutable binder mixtures based on alkyd resins and poly-n-acyl alkyleneimines

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- Number: US 5,344,859 A
- Document ID: US5344859A
- Status: Granted
- Kind: A
- Application number: 07/866,161
- Filed: 1992-08-07
- Granted: 1994-09-06
- Earliest claimed: 1989-12-27
- Assignees: Henkel Kommanditgesellschaft auf Aktien
- Inventors: Ulrich Eicken; Brigitte Hase; Manfred Gorzinski; Wolfgang Gress; Norbert Stork
- Web page: https://patentgrep.com/patent/US5344859A

## CPC

- C09D 167/08: Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
- C08G 63/66: Polyesters containing oxygen in the form of ether groups (C08G63/42, C08G63/58 take precedence)
- C08L 79/02: Polyamines
- C09D 179/02: Polyamines
- C08L 67/08: Polyesters modified with higher fatty oils or their acids, or with resins or resin acids
- 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
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

This invention includes new water-dilutable binder mixtures based on alkyd resins modified by poly{ethylene glycol} and poly{N-acyl alkylene imines}, a process for preparing such binder mixtures, and the use of such binders in oxidatively drying paints and varnishes.

## Claims

### Claim 1

Water-dilutable binder mixtures that are suitable for oxidatively drying paints, said binder mixtures comprising alkyd resins in which polyethylene glycol is incorporated and of which the residual acid groups have been at least partly neutralized by addition of bases, wherein the improvement comprises the presence in the binder mixtures of poly-N-acyl alkyleneimines prepared by cationic polymerization of at least two chemically distinct types of monomers corresponding to general formula I: ##STR3## in which Z is a direct bond or the group ##STR4## where R.sup.5 and R.sup.6 may be the same or different and represent H or alkyl containing up to 2 carbon atoms,
R.sup.1 to R.sup.4 may be the same or different and represent H, or an aromatic radical or aliphatic radical, each containing up to 8 carbon atoms, and
R.sup.7 is an aromatic or aliphatic radical, attached by carbon, containing up to 21 carbon atoms,
wherein from 5 to 50% by weight of the monomers corresponding to general formula I have an aromatic radical as R.sup.7, from 25 to 95% by weight of the monomers corresponding to general formula I have an olefinically unsaturated radical as R.sup.7, and not more than 25% by weight of the monomers corresponding to general formula I have a saturated alkyl group as R.sup.7.

### Claim 2 (depends on 1)

Binder mixtures as claimed in claim 1, wherein the poly-N-acyl alkyleneimines present in the binder mixtures have been produced from monomers corresponding to general formula I in which all the substituents R.sup.1 to R.sup.4 are hydrogen atoms and Z is a direct bond.

### Claim 3 (depends on 2)

Binder mixtures as claimed in claim 2, which contain poly-N-acyl alkyleneimines which have been produced by polymerization of a mixture of monomers comprising from 10 to 30% by weight of monomers with an aromatic moiety in R.sup.7 and from 50 to 90% by weight of monomers with an olefinically unsaturated moiety in R.sup.7, and, optionally up to 25% by weight of monomers with a saturated alkyl group as R.sup.7.

### Claim 4 (depends on 3)

Binder mixtures as claimed in claim 3, wherein the alkyd resin component has been produced by reacting monobasic and polybasic carboxylic acids, anhydrides thereof, or mixtures of acids and anhydrides with polyhydric alcohols including polyethylene glycol in quantities below 15% by weight, based on the mixture of alkyd-resin-forming reactants.

### Claim 5 (depends on 4)

Binder mixtures as claimed in claim 4, wherein more than 50% of the residual acid groups of the alkyd resins are neutralized and the alkyd resins have a residual acid value above 5 and below 20, expressed as free and neutralized carboxylic acid groups.

### Claim 6 (depends on 5)

Binder mixtures as claimed in claim 5, wherein the residual acid groups of the alkyd resins are at least partly neutralized with volatile amines, ammonia, or a mixture of ammonia and at least one volatile amine.

### Claim 7 (depends on 6)

Binder mixtures as claimed in claim 6, comprising alkyd resins in quantities of 50 to 75% by weight in admixture with, bonded to, or both in admixture with and bonded to, poly-N-acyl alkyleneimines in quantities of 25 to 50% by weight, based on the binder mixture.

### Claim 8 (depends on 1)

A process for the production of the binder mixtures claimed in claim 1, wherein the monomers corresponding to general formula I are polymerized in alkyd resin to form poly-N-acyl alkyleneimines, and, optionally, the reaction mixture obtained after polymerization of the monomers in the alkyd resin is reacted with dicarboxylic acids, anhydrides thereof, or a mixture of any two or more dicarboxylic acids and/or anhydrides of dicarboxylic acids.

### Claim 9 (depends on 7)

A paint comprising binders as claimed in claim 7 in quantities of 20% by weight to 40% by weight, expressed as solids and based on paint.

### Claim 10 (depends on 1)

Binder mixtures as claimed in claim 1, wherein the poly-N-acyl alkyleneimines present in the binder mixtures have been produced from monomers corresponding to general formula I in which the substituents R.sup.1 to R.sup.4 may be the same or different and represent H or alkyl radicals containing up to 3 carbon atoms, at least two of the substituents being hydrogen atoms.

### Claim 11 (depends on 1)

Binder mixtures as claimed in claim 1, wherein the alkyd resin component has been produced by reacting monobasic and polybasic carboxylic acids, anhydrides thereof, or mixtures of acids and anhydrides with polyhydric alcohols including polyethylene glycol in quantities below 15% by weight, based on the mixture of alkyd-resin-forming reactants.

### Claim 12 (depends on 1)

Binder mixtures as claimed in claim 1, wherein more than 50% of the residual acid groups of the alkyd resins are neutralized and the alkyd resins have a residual acid value above 5 and below 25, expressed as free and neutralized carboxylic acid groups.

### Claim 13 (depends on 1)

Binder mixtures as claimed in claim 1, wherein the residual acid groups of the alkyd resins are at least partly neutralized with volatile bases.

### Claim 14 (depends on 1)

Binder mixtures as claimed in claim 1, comprising alkyd resins in quantities of 10 to 90% by weight in admixture with, bonded to, or both in admixture with and bonded to, poly-N-acyl alkyleneimines in quantities of 10 to 90% by weight, based on the binder mixture.

### Claim 15 (depends on 1)

A paint comprising binders as claimed in claim 1 in quantities of 20% by weight to 40% by weight, expressed as solids and based on paint.

### Claim 16 (depends on 6)

A paint comprising binders as claimed in claim 6 in quantities of 20% by weight to 40% by weight, expressed as solids and based on paint.

### Claim 17 (depends on 5)

A paint comprising binders as claimed in claim 5 in quantities of 20% by weight to 40% by weight, expressed as solids and based on paint.

### Claim 18 (depends on 2)

A paint comprising binders as claimed in claim 2 in quantities of 15% by weight to 50% by weight, expressed as solids and based on paint.

### Claim 19 (depends on 1)

A paint comprising binders as claimed in claim 1 in quantities of 15% by weight to 50% by weight, expressed as solids and based on paint.