# US 5,705,597 A · Ketone-aldehyde resin with wide compatibility, process for its preparation, and composition containing same

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- Number: US 5,705,597 A
- Document ID: US5705597A
- Status: Granted
- Kind: A
- Application number: 08/388,283
- Filed: 1995-02-14
- Granted: 1998-01-06
- Earliest claimed: 1994-02-16
- Assignees: Huels Aktiengesellschaft
- Inventors: Martina Ortelt; Werner Freitag; Christina Machate
- Web page: https://patentgrep.com/patent/US5705597A

## CPC

- C09D 17/002: {in organic medium (C09D17/003, C09D17/004 take precedence)}
- C08G 6/02: of aldehydes with ketones
- C09D 7/65: macromolecular (C09D7/41-C09D7/48 take precedence)
- C08L 61/02: Condensation polymers of aldehydes or ketones only
- Y10S 525/934: Powdered coating composition
- Y10T 428/31594: Next to aldehyde or ketone condensation product [phenol-aldehyde, etc.]
- 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)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Ketone-aldehyde resins with wide compatibility, process for their preparation, and their use. The invention relates to ketone-aldehyde resins with wide compatibility comprising cycloaliphatic ketones and, in particular, formaldehyde and, if desired, further monomers, to a process for their preparation and to their use as hard resin in paints, printing inks and other coatings, especially in pigment preparations.

## Claims

### Claim 1

A ketone-aldehyde condensation resin consisting essentially of:
A) a ketone component:
i) 40 to 100 mol % of at least one C.sub.1-8 alkyl-substituted cyclohexanone having one or more C.sub.1-8 alkyl radicals; and
ii) 0 to 60 mol % of a further ketone other than i) having C.sub.1-20 aliphatic, C.sub.3-20 cycloaliphatic, C.sub.6-30 aromatic hydrocarbon radicals, substituted C.sub.1-20 aliphatic, substituted C.sub.3-20 cycloaliphatic, substituted C.sub.6-30 aromatic hydrocarbon radicals wherein said substituents are C.sub.1-20 aliphatic, C.sub.3-20 cycloaliphatic, C.sub.6-30 aromatic hydrocarbon radicals; and
B) 0.8 to 2.0 mol of at least one C.sub.1-20 aliphatic aldehyde per mole of all the ketones employed,
wherein said resin has an average molecular weight (Mn) of from 500 to 1,000 and a softening point of from 70.degree. to 95.degree. C.

### Claim 2 (depends on 1)

The ketone-aldehyde resin of claim 1, wherein said alkyl-substituted cyclohexanone is selected from the group consisting of 4-tert-butylcyclohexanone, 3,3,5-trimethylcyclohexanone and a mixture thereof.

### Claim 3 (depends on 1)

The ketone-aldehyde resin of claim 1, wherein said C.sub.1-20 aliphatic aldehyde is selected from the group consisting of formaldehyde, acetaldehyde, butyraldehyde, dodecanal and a mixture thereof.

### Claim 4 (depends on 1)

The ketone-aldehyde resin of claim 1, wherein said aliphatic aldehyde is formaldehyde.

### Claim 5 (depends on 1)

The ketone-aldehyde resin of claim 1, wherein said further ketone is selected from the group consisting of acetophenone, methyl ethyl ketone, cyclohexanone and a mixture thereof.

### Claim 6 (depends on 1)

The ketone-aldehyde resin of claim 1 wherein said ketone component consists of a mixture of 3,3,5-trimethylcyclohexanone, 4-tertbutylcyclohexanone and/or cyclohexanone.

### Claim 7 (depends on 1)

A coating system comprising:
i) the ketone-aldehyde resin of claim 1; and
ii) a solvent.

### Claim 8 (depends on 1)

A pigment concentrate or tinting paste comprising:
i) the ketone-aldehyde resin of claim 1; and
ii) a pigment.

### Claim 9

A process for the preparation of a condensation ketone-aldehyde resin, comprising condensing a mixture consisting essentially of
A) a ketone component:
i) 40 to 100 mol % of at least one C.sub.1-8 alkyl-substituted cyclohexanone having one or more C.sub.1-8 alkyl radicals; and
ii) 0 to 60 mol % of a further ketone other than i) having C.sub.1-20 aliphatic, C.sub.3-20 cycloaliphatic, C.sub.6-30 aromatic hydrocarbon radicals, substituted C.sub.1-20 aliphatic, substituted C.sub.3-20 cycloaliphatic, substituted C.sub.6-30 aromatic hydrocarbon radicals wherein said substituents are C.sub.1-20 aliphatic, C.sub.3-20 cycloaliphatic, C.sub.6-30 aromatic hydrocarbon radicals; and
B) 0.8 to 2.0 mol of at least one C.sub.1-20 aliphatic aldehyde per mole of all the ketones employed
in the presence of alkaline catalysts at temperatures of from 80.degree. to 90.degree. C.,
wherein said resin has an average molecular weight (Mn) of from 500 to 1,000 and a softening point of from 70.degree. to 95.degree. C.

### Claim 10 (depends on 1)

The ketone-aldehyde resin of claim 1, wherein said condensation is carried out in the presence of an alkaline catalyst.

### Claim 11

A ketone-aldehyde condensation resin consisting essentially of:
A) a ketone component:
i) 40 to 100 mol % of at least one C.sub.1-8 alkyl-substituted cyclohexanone having one or more C.sub.1-8 alkyl radicals; and
ii) 0 to 60 mol % of a further ketone other than i) having C.sub.1-20 aliphatic, C.sub.3-20 cycloaliphatic, C.sub.6-30 aromatic hydrocarbon radicals, substituted C.sub.1-20 aliphatic, substituted C.sub.3-20 cycloaliphatic, substituted C.sub.6-30 aromatic hydrocarbon radicals wherein said substituents are C.sub.1-20 aliphatic, C.sub.3-20 cycloaliphatic, C.sub.6-30 aromatic hydrocarbon radicals; and
B) 0.8 to 2.0 mol of at least one C.sub.1-20 aliphatic aldehyde per mole of all the ketones employed, and
C) up to 60 mol % of phenol, phenol derivatives, urea, urea derivatives or mixtures thereof,
wherein said resin has an average molecular weight (Mn) of from 500 to 1,000 and a softening point of from 70.degree. to 95.degree. C.

### Claim 12

A ketone-aldehyde condensation resin consisting essentially of:
A) a ketone component:
i) 40 to 100 mol % of at least one C.sub.1-8 alkyl-substituted cyclohexanone having one or more C.sub.1-8 alkyl radicals; and
ii) 0 to 60% of a further ketone other than i) having C.sub.1-20 aliphatic, C.sub.3-20 cycloaliphatic, C.sub.6-30 aromatic hydrocarbon radicals, substituted C.sub.1-20 aliphatic, substituted C.sub.3-20 cycloaliphatic, substituted C.sub.6-30 aromatic hydrocarbon radicals wherein said substituents are C.sub.1-20 aliphatic, C.sub.3-20 cycloaliphatic, C.sub.6-30 aromatic hydrocarbon radicals; and
B) 0.8 to 2.0 mol of a mixture of formaldehyde and benzaldehyde of all the ketones employed,
wherein said resin has an average molecular weight (Mn) of from 500 to 1,000 and a softening point of from 70.degree. to 95.degree. C.