# US 8,569,438 B2 · Coating agents having high scratch resistance and weathering stability

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- Number: US 8,569,438 B2
- Document ID: US8569438B2
- Status: Granted
- Kind: B2
- Application number: 12/519,458
- Filed: 2007-12-19
- Published: 2010-06-10
- Granted: 2013-10-29
- Earliest claimed: 2006-12-19
- Assignees: BASF Coatings GmbH
- Applicants: Matthijs Groenewolt; Andreas Poppe; Guenter Klein; Manuela Niemeier; Elke Westhoff; Wilfried Stuebbe; Simone Hesener
- Inventors: Matthijs Groenewolt; Andreas Poppe; Guenter Klein; Manuela Niemeier; Elke Westhoff; Wilfried Stuebbe; Simone Hesener
- Web page: https://patentgrep.com/patent/US8569438B2

## CPC

- C09D 175/14: Polyurethanes having carbon-to-carbon unsaturated bonds
- C08G 18/289: {containing silicon}
- C08G 18/6254: {Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups}
- C08G 18/778: {silicon}
- C08G 18/809: {containing silicon}
- C09D 175/04: Polyurethanes
- 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

## Abstract

Disclosed are coating compositions comprising (a) at least one hydroxyl-containing compound (A), (b) at least one compound (B) having isocyanate groups, and (c) at least one catalyst (D) for the crosslinking of silane groups, said catalyst (D) comprising phosphorus. It is an aspect of the disclosed coating compositions that (i) one or more constituents of the coating composition contain hydrolyzable silane groups and (ii) the coating composition can be finally cured to a coating which has statistically distributed regions of an Si—O—Si network.

## Claims

### Claim 1

A coating composition comprising
(a) at least one hydroxyl-containing compound (A),
(b) at least one compound (B) having free and/or blocked isocyanate groups,
(c) at least one catalyst (D) for the crosslinking of silane groups, said catalyst (D) comprising phosphorus and nitrogen, and said catalyst (D) being blocked with a tertiary amine
where
(i) one or more constituents of the coating composition contain hydrolyzable silane groups and
(ii) the coating composition can be finally cured to a coating which has statistically distributed regions of an Si-O-Si network.

### Claim 2 (depends on 1)

The coating composition of claim 1, wherein the at least one catalyst (D) is selected from the group consisting of substituted phosphonic diesters, substituted diphosphonic diesters, substituted phosphoric monoesters, substituted phosphoric diesters and mixtures thereof.

### Claim 3 (depends on 1)

The coating composition of claim 1, wherein the catalyst (D) is selected from the group consisting of amine-blocked phosphoric acid ethylhexyl partial esters and amine-blocked phosphoric acid phenyl partial esters.

### Claim 4 (depends on 1)

The coating composition of claim 1, wherein one or more constituents of the coating composition comprise at least one or more, identical or different structural units of the formula (I)
—X—Si—RxG3-x (I)
where
G =identical or different hydrolyzable groups, X =linear and/or branched alkylene or cycloalkylene radical having 1 to 20 carbon atoms, R″ =alkyl, cycloalkyl, aryl or aralkyl, in which a carbon chain may comprise nonadjacent oxygen, sulfur or NRa groups, with Ra =alkyl, cycloalkyl, aryl or aralkyl,
x =0 to 2.

### Claim 5 (depends on 1)

A coating composition of claim 1 wherein one or more constituents of the coating composition comprise between 2.5 and 97.5 mol %, based on the entirety of structural units (II) and (III), of at least one structural unit of the formula (II)
—N(X—SiR″x(OR′)3-x)n(X′—SiR″y(OR′)3-y)m (II)
where
R′ =hydrogen, alkyl or cycloalkyl, in which a carbon chain may comprise nonadjacent oxygen, sulfur or NRa groups, with Ra =alkyl, cycloalkyl, aryl or aralkyl,
X, X′ =linear and/or branched alkylene or cycloalkylene radical having 1 to 20 carbon atoms,
R″ =alkyl, cycloalkyl, aryl or aralkyl, in which a carbon chain may comprise nonadjacent oxygen, sulfur or NRa groups, with Ra =alkyl, cycloalkyl, aryl or aralkyl,
n =0 to 2, m =0 to 2, m+n =2, and x =0 to 2, y =0 to 2, and
between 2.5 and 97.5 mol %, based on the entirety of structural units (II) and (III), of at least one structural unit of the formula (III)
—Z—(X—SiR″x(OR′)3-x) (III),
where
Z =—NH—, —NR—, —0—, with
R =alkyl, cycloalkyl, aryl or aralkyl, in which a carbon chain may comprise nonadjacent oxygen, sulfur or NRa groups, with Ra =alkyl, cycloalkyl, aryl or aralkyl,
x =0 to 2, and
X, R′, R″ have the meaning given in formula (II).

### Claim 6 (depends on 5)

The coating composition of claim 5, wherein one or more constituents of the coating composition contain between 5 and 95 mol%, based on the entirety of the structural units (II) and (III), of at least one structural unit of the formula (II), and between 5 and 95 mol %, based on the entirety of the structural units (II) and (III), of at least one structural unit of the formula (III).

### Claim 7 (depends on 6)

The coating composition of claim 6, wherein the structural elements (II) and (III) are present in fractions of 2.5 to 97.5 mol %, based on the sum of the functional groups critical for crosslinking in the coating composition, formed from the fractions of the hydroxyl and isocyanate groups and from the fractions of the structural elements (II) and (III).

### Claim 8 (depends on 7)

The coating composition of claim 7, wherein the coating composition contains less than 6.5% by mass of Si of the structural units (II) and/or (III), based in each case on the solids content of the coating composition.

### Claim 9 (depends on 5)

The coating composition of claim 5, wherein the polyisocyanate (B) comprises the structural units (II) or (III).

### Claim 10 (depends on 9)

The coating composition of claim 9, wherein, the polyisocyanate (B) comprises a core polyisocyanate structure and in the polyisocyanate (B),
between 2.5 and 90 mol % of the isocyanate groups in the core polyisocyanate structure have undergone reaction to structural units (II) and
between 2.5 and 90 mol % of the isocyanate groups in the core polyisocyanate structure have undergone reaction to structural units (III)
and/or the total fraction of the isocyanate groups in the core polyisocyanate structure that have undergone reaction to structural units (II) and/or (III) is between 5 and 95 mol %.

### Claim 11 (depends on 9)

The coating composition of claim 9, wherein the polyisocyanate (B) comprises a core polyisocyanate structure selected from the group consisting of 1,6-hexamethylene diisocyanate, isophorone diisocyanate, and 4,4′-methylenedicyclohexyl diisocyanate, the biuret dimers of the aforementioned polyisocyanates, the isocyanurate trimers of the aforementioned polyisocyanates, and mixtures thereof.

### Claim 12 (depends on 1)

The coating composition of claim 1, wherein the polyol (A) comprises at least one poly(meth)acrylate polyol.

### Claim 13 (depends on 1)

A multistage coating method which comprises applying a pigmented basecoat film to an uncoated or precoated substrate and thereafter applying a film of the coating composition of claim 1.

### Claim 14 (depends on 1, 13)

The multistage coating method of claim 13, wherein, following the application of the pigmented basecoat film, the applied basecoat material is first dried at temperatures from room temperature to 80° C. and, following the application of the coating composition of claim 1, the system is cured at temperatures from 30 to 200° C. for a time of 1 min up to 10 h.

### Claim 15 (depends on 1)

The coating composition of claim 1 that is a clearcoat material for automotive OEM finishing or automotive refinish.

### Claim 16 (depends on 1)

The coating composition of claim 1, wherein the at least one catalyst (D) is selected from the group consisting of acyclic phosphoric diesters, cyclic phosphoric diesters and mixtures thereof.

### Claim 17 (depends on 1)

The coating composition of claim 1, wherein the catalyst (D) is amine-blocked bis(ethylhexyl) phosphate.

### Claim 18

A coating composition comprising:
(a) at least one hydroxyl-containing compound (A),
(b) at least one compound (B) having free and/or blocked isocyanate groups,
(c) at least one catalyst (D) for the crosslinking of silane groups, said catalyst (D) comprising phosphorus and nitrogen,
where
(i) one or more constituents of the coating composition contain hydrolyzable silane groups and
(ii) the coating composition can be finally cured to a coating which has statistically distributed regions of an Si-O-Si network
(iii) one or more constituents of the coating composition comprise between 2.5 and 97.5 mol %, based on the entirety of structural units (II) and (III), of at least one structural unit of the formula (II)
—N(X—SiR″x(OR′)3-x)n(X′—SiR″y(OR')3-y)m (II)
where
R′ =hydrogen, alkyl or cycloalkyl, in which a carbon chain may comprise nonadjacent oxygen, sulfur or NRa groups, with Ra =alkyl, cycloalkyl, aryl or aralkyl,
X, X′ =linear and/or branched alkylene or cycloalkylene radical having 1 to 20 carbon atoms,
R″ =alkyl, cycloalkyl, aryl or aralkyl, in which a carbon chain may comprise nonadjacent oxygen, sulfur or NRa groups, with Ra =alkyl, cycloalkyl, aryl or aralkyl,
n =0 to 2, m =0 to 2, m+n =2, and x =0 to 2, y =0 to 2, and
between 2.5 and 97.5 mol%, based on the entirety of structural units (II) and (III), of at least one structural unit of the formula (III)
—Z—(X—SiR″x(OR′)3-x) (III),
where
Z =—NH—, —NR—, —0—, with
R =alkyl, cycloalkyl, aryl or aralkyl, in which a carbon chain may comprise nonadjacent oxygen, sulfur or NRa groups, with Ra =alkyl, cycloalkyl, aryl or aralkyl,
x =0 to 2, and
X, R′, R″ have the meaning given in formula (II).

### Claim 19

A coating composition comprising:
(a) at least one hydroxyl-containing compound (A),
(b) at least one compound (B) having free and/or blocked isocyanate groups,
(c) at least one catalyst (D) for the crosslinking of silane groups, said catalyst (D) being an amine-blocked bis(ethylhexyl) phosphate
where
(i) one or more constituents of the coating composition contain hydrolyzable silane groups and
(ii) the coating composition can be finally cured to a coating which has statistically distributed regions of an Si—O—Si network.