# US 2017/0253752 A1 · Coating Composition Comprising Anti-Skinning Agent

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- Number: US 2017/0253752 A1
- Document ID: US20170253752A1
- Status: Published application
- Kind: A1
- Application number: 15/517,930
- Filed: 2014-10-09
- Published: 2017-09-07
- Earliest claimed: 2014-10-09
- Assignees: PPG Coatings Europe B.V.
- Applicants: PPG Europe B.V.
- Inventors: John Weijnen; Cornelis Brandjes
- Web page: https://patentgrep.com/patent/US20170253752A1

## CPC

- C09D 7/46: Anti-skinning agents
- C08G 18/4288: {modified by higher fatty oils or their acids or by resin acids}
- C09D 167/08: Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
- C08K 5/07: Aldehydes; Ketones
- C08K 5/33: Oximes
- 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
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

The invention relates to a coating composition comprising an oxidatively drying binder and an anti-skinning agent, the anti-skinning agent comprising: a) a diketone of formula (I) (b) an aldoxime or ketoxime of formula (II) wherein R1, R2, R3, R4 and n have the same meaning as that defined by the present application.

## Claims

### Claim 1

A coating composition comprising an oxidatively drying binder and an anti-skinning agent, the anti-skinning agent comprising:
a) a diketone of formula I
wherein
n is an integer selected from 1 and 2, preferably wherein n is 1; and
R1 is selected from the group comprising C1-24alkyl, C6-20aryl, C6-20arylC1-12alkyl, heteroaryl, heteroarylC1-12alkyl, each group being optionally substituted with one or more substituents each independently selected from the group comprising C1-6alkyl, —OH, and halogen;
R2 is selected from the group comprising C1-24alkyl, C6-20aryl, C6-20arylC1-12alkyl, heteroaryl, heteroarylC1-12alkyl, each group being optionally substituted with one or more substituents each independently selected from the group comprising C1-6alkyl, —OH, and halogen; or
R1 taken together with R2 form a 4, 5, 6, 7, 8, 9 or 10-membered carbon ring, optionally substituted with one or more substituents each independently selected from the group comprising C1-6alkyl, —OH, and halogen;
b) an aldoxime or ketoxime of formula II
wherein
R3 is hydrogen or is selected from the group comprising C1-24alkyl, C6-20aryl, C6-20arylC1-12alkyl, heteroaryl, heteroarylC1-12alkyl, each group being optionally substituted with one or more substituents each independently selected from the group comprising C1-6alkyl, —OH, and halogen;
R4 is hydrogen or is selected from the group comprising C1-24alkyl, C6-20aryl, C6-20arylC1-12alkyl, heteroaryl, heteroarylC1-12alkyl, each group being optionally substituted with one or more substituents each independently selected from the group comprising C1-6alkyl, —OH, and halogen; or
R3 taken together with R4 form a 5, 6, 7, 8, 9 or 10-membered carbon ring, optionally substituted with one or more substituents each independently selected from the group comprising C1-6alkyl, —OH, and halogen.

### Claim 2 (depends on 1)

The coating composition according to claim 1, the coating composition further comprising at least one metal complex comprising at least one metal, wherein the at least one metal is selected from the group comprising cobalt (Co), manganese (Mn), iron (Fe), vanadium (V), cerium (Ce), copper (Cu), lead (Pb), calcium (Ca), zirconium (Zr), lanthanum (La), neodymium (Nd), bismuth (Bi), strontium (Sr), zinc (Zn), lithium (Li), potassium (K), and barium (Ba), preferably wherein the at least one metal is selected from the group comprising cobalt (Co), manganese (Mn), iron (Fe), vanadium (V), cerium (Ce), copper (Cu), and lead (Pb).

### Claim 3 (depends on 2)

The coating composition according to claim 2, wherein the metal complex is a metal salt of an organic acid, preferably a cobalt (Co) salt of an organic acid, a calcium (Ca) salt of an organic acid, or a zirconium (Zr) salt of an organic acid.

### Claim 4 (depends on 1, 2, 3)

The coating composition according to claim any one of claims 1 to 3, wherein R1 is methyl and R2 is methyl.

### Claim 5 (depends on 1, 2, 3, 4)

The coating composition according to claim any one of claims 1 to 4, wherein n is 1.

### Claim 6 (depends on 1, 2, 3, 4, 5)

The coating composition according to claim any one of claims 1 to 5, wherein the diketone of formula (I) is 2,4-pentanedione.

### Claim 7 (depends on 1, 2, 3, 4, 5, 6)

The coating composition according to claim any one of claims 1 to 6, wherein the diketone of formula (I) is present in a concentration of at least 0.5% by weight, with % by weight based on the total weight of the coating composition.

### Claim 8 (depends on 1, 2, 3, 4, 5, 6, 7)

The coating composition according to claim any one of claims 1 to 7, wherein the aldoxime or ketoxime of formula (II) is selected from the group comprising methyl ethyl ketoxime, dimethyl ketoxime, cyclohexanone oxime, methyl isobutyl ketoxime, formaldehyde oxime, acetaldehyde oxime, propionaldehyde oxime, butyraldehyde oxime, isobutyraldehyde oxime, pentan-2-one oxime, pentan-3-one oxime, cyclopentanone oxime, 3-methylbutyraldehyde oxime, hexan-2-one oxime, heptanal oxime, heptan-2-one oxime, heptan-3-one oxime, heptan-4-one oxime, 2,4-dimethylpentan-3-one oxime, 5-methylhexan-2-one oxime, benzaldehyde oxime, salicylaldoxime, acetophenone oxime, benzophenone oxime, 3-pyridinealdoxime, and 4-pyridinealdoxime.

### Claim 9 (depends on 1, 2, 3, 4, 5, 6, 7, 8)

The coating composition according to claim any one of claims 1 to 8, wherein the aldoxime or ketoxime of formula (II) is present in a concentration of at most 0.40% by weight, with % by weight based on the total weight of the coating composition.

### Claim 10

The coating composition or use according to any one of statements 1 to 9, wherein the aldoxime or ketoxime of formula (II) is present in a concentration of at least 0.01% by weight, with % by weight based on the total weight of the coating composition.

### Claim 11 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10)

The coating composition according to any one of claims 1 to 10, wherein the oxidatively drying binder is an alkyd binder.

### Claim 12 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11)

The coating composition according to any one of claims 1 to 11, wherein the coating composition is substantially free of aluminium.

### Claim 13

Use of a composition comprising:
a) a diketone of formula I
wherein
n is an integer selected from 1 and 2, preferably wherein n is 1; and
R1 is selected from the group comprising C1-24alkyl, C6-20aryl, C6-20arylC1-12alkyl, heteroaryl, heteroarylC1-12alkyl, each group being optionally substituted with one or more substituents each independently selected from the group comprising C1-6alkyl, —OH, and halogen;
R2 is selected from the group comprising C1-24alkyl, C6-20aryl, C6-20arylC1-12alkyl, heteroaryl, heteroarylC1-12alkyl, each group being optionally substituted with one or more substituents each independently selected from the group comprising C1-6alkyl, —OH, and halogen; or
R1 taken together with R2 form a 4, 5, 6, 7, 8, 9 or 10-membered carbon ring, optionally substituted with one or more substituents each independently selected from the group comprising C1-6alkyl, —OH, and halogen; and
b) an aldoxime or ketoxime of formula II
wherein
R3 is hydrogen or is selected from the group comprising C1-24alkyl, C6-20aryl, C6-20arylC1-12alkyl, heteroaryl, heteroarylC1-12alkyl, each group being optionally substituted with one or more substituents each independently selected from the group comprising C1-6alkyl, —OH, and halogen;
R4 is hydrogen or is selected from the group comprising C1-24alkyl, C6-20aryl, C6-20arylC1-12alkyl, heteroaryl, heteroarylC1-12alkyl, each group being optionally substituted with one or more substituents each independently selected from the group comprising C1-6alkyl, —OH, and halogen; or
R3 taken together with R4 form a 5, 6, 7, 8, 9 or 10-membered carbon ring, optionally substituted with one or more substituents each independently selected from the group comprising C1-6alkyl, —OH, and halogen;
as an anti-skinning agent in a coating composition comprising an oxidatively drying binder.

### Claim 14 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12)

Use of a coating composition according any one of claims 1 to 12, in a varnish, lacquer, paint, stain, enamel, printing ink, or floor covering.

### Claim 15 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12)

A substrate having applied thereon a coating composition according to any one of claims 1 to 12.