Coating agents having improved runoff tendency

Patent metadata

Field	Value
Publication number	US-9404011-B2
Application number	US-201113642630-A
Country	US
Kind code	B2
Filing date	Mar 30, 2011
Priority date	Apr 21, 2010
Publication date	Aug 2, 2016
Grant date	Aug 2, 2016

Abstract

Coating compositions comprising at least one hydroxyl-containing compound (A), at least one isocyanato-containing compound (B) and at least one urea-group-containing compound (H) different from (B), compound (H) comprising at least one structural unit selected from the group consisting of a structural unit (I)

a structural unit (II)

a structural unit (III)

—NR′″—C(O)—N(X—SiR″ x (OR′) 3-x ) n (X′—SiR″ y (OR′) 3-y ) m , and combinations of two or more of the foregoing, compound (H) being obtained by reacting an isocyanato-containing compound (H G ) with amino-containing compounds, wherein in compound (H) more than 90 mol % of the isocyanate groups originally present in (H G ) have undergone reaction to form the structural units (I), (II), (III), or combinations thereof, where R′, R′″=hydrogen, alkyl, cycloalkyl, aryl or aralkyl; R, R″=alkyl, cycloalkyl, aryl or aralkyl; X, X′=linear and/or branched alkyl or cycloalkyl radical; x, y, n, m=0 to 2; and m+n=2.

First claim

The invention claimed is:

1. A coating composition based on aprotic solvents, comprising at least one hydroxyl-containing compound (A), at least one isocyanato-containing compound (B), and at least one urea-group containing compound (H) different from the compound (B),
wherein
(i) the urea-group-containing compound (H) comprises at least one structural unit of the formula (I):

and at least one other structural unit, said other structural unit being selected from the group consisting of
(a) at least one structural unit (II) of the following formula (II)

(b) at least one structural unit (III) of the following formula (III)
—NR′″—C(O)—N(X—SiR″ x (OR′) 3-x ) n (X′—SiR″ y (OR′) 3-y ) m   (III)

and
(c) at least one structural unit (II) of the formula (II) and at least one structural unit (III) of the formula (III), and
(ii) the urea-group-containing compound (H) is obtained by reacting an isocyanato-containing compound (H G ) with amino-containing compounds, and
(iii) in the urea-group-containing compound (H) more than 90 mol % of the isocyanate groups originally present in the isocyanato-containing compound (H G ) have undergone reaction to form the structural units (I) and (II), or (I) and (III), or (I) and (II) and (III),
wherein, in the formulae (I), (II), and (III)
R′″=hydrogen, alkyl, cycloalkyl, aryl or aralkyl, it being possible for the carbon chain to be interrupted by nonadjacent oxygen, sulfur or NRa groups, with Ra=alkyl, cycloalkyl, aryl or aralkyl,
R,R″=alkyl, cycloalkyl, aryl or aralkyl, it being possible for the carbon chain to be interrupted by nonadjacent oxygen, sulfur or NRa groups, with Ra=alkyl, cycloalkyl, aryl or aralkyl,
R′=hydrogen, alkyl or cycloalkyl, it being possible for the carbon chain to be interrupted by nonadjacent oxygen, sulfur or NRa groups,
X, X′=linear and/or branched alkyl or cycloalkyl radical having 1 to 20 carbon atoms,
x=0 to 2, y=0 to 2, and n=0 to 2, m=0 to 2, and m+n=2.

2. The coating composition of claim 1 , wherein the compound (H) has at least one structural unit of the formula (I), at least one structural unit of the formula (II) and at least one structural unit of the formula (III).

3. The coating composition of claim 2 , wherein the compound (H) comprises from 10 and 60 mol %, based in each case on the entirety of the structural units (I), (II), and (III), of at least one structural unit of the formula (I), and the sum of the structural units (II) plus structural units (III) is between 90 and 40 mol %, based in each case on the entirety of the structural units (I), (II) and (III).

4. The coating composition of claim 1 , wherein, in the compound (H), more than 95 mol %, of the isocyanate groups originally present have undergone reaction to form the structural units (I) and (II) or (I) and (III) or (I) and (II) and (III).

5. The coating composition of claim 1 , wherein the compound (H) is prepared by reacting an isocyanato-containing compound (H G ) with a primary monoalkoxysilylamine (Ia) of the formula (Ia)
H 2 N—(X—SiR″ x (OR′) 3-x )  (Ia),

and
with a member selected from the group consisting of a secondary monoalkoxysilylamine (IIa) of the formula (IIa)

a bisalkoxysilylamine of the formula (IIIa)
HN(X—SiR″ x (OR′) 3-x ) n (X′—SiR″ y (OR′) 3-y ) m   (IIa),

and combinations thereof,
where R, R′, X, X′, R″ x, y, m and n are as defined above.

6. The coating composition of claim 1 , wherein the isocyanato-containing compound (HG) is an isocyanurate trimer of an aliphatic and/or cycloaliphatic diisocyanate.

7. The coating composition of claim 1 , wherein the isocyanate-containing compound (H G ) is selected from the group consisting of 1,6-hexamethylene diisocyanate, 4,4′-methylenedicyclohexyl diisocyanate, the isocyanurate trimers of the aforementioned polyisocyanates, and combinations of the two or more of the foregoing.

8. The coating composition of claim 1 , comprising from 1% to 20%, based in each case on the nonvolatile constituents of its component (B), of at least one urea-containing compound (H).

9. The coating composition of claim 1 , wherein one or more constituents of the coating composition that are different from the compound (H) comprise at least one structural unit selected from the group consisting of
a structural unit (IV) of the formula (IV)

a structural unit (V) of the formula (V)
—N(X—SiR″ x (OR′) 3-x ) n (X′—SiR″ y (OR′) 3-y ) m   (V),

and combinations of the foregoing, where R, R′, X, X′, R″ x, y, m and n are as defined above.

10. The coating composition of claim 1 , wherein at least part of the isocyanato-containing compound (B) has at least one structural unit of the formula (IV) and at least one structural unit of the formula (V).

11. The coating composition of claim 10 , wherein, in the isocyanato-containing compound (B), between 0 and 90 mol % of the isocyanate groups in the polyisocyanate parent structure have undergone reaction to form structural units (IV) and/or between 0 and 90 mol % of the isocyanate groups in the polyisocyanate parent structure have undergone reaction to form structural units (V), and/or the total fraction of the isocyanate groups in the polyisocyanate parent structure that have undergone reaction to form the structural units (IV) and (V) is between 0 and 90 mol %.

12. The coating composition of claim 1 , wherein the at least one hydroxyl-containing compound (A) comprises at least one poly(meth)acrylate polyol and/or at least one hydroxy-functional polyester in which on average at least one hydroxyl function of the polyester is esterified with at least one acid selected from the group of the isomeric C8 to C9 monocarboxylic acids.

13. A multistage coating method comprising applying a pigmented basecoat film to an optionally precoated substrate and thereafter applying a film of a coating composition as claimed in claim 1 .

14. An effect and/or color paint system comprising at least one pigmented coating with a clearcoat disposed thereon, wherein the clearcoat has been produced from a coating composition as claimed in claim 1 .

15. The method of claim 13 wherein the substrate is selected from automotive OEM finishing substrates, commercial vehicle finishing substrates, refinish substrates, bodywork component substrates, interior installation substrates, exterior installation substrates, and combinations of the foregoing.

Assignees

• Groenewolt Matthijs
• Niemeier Manuela
• Basf Coatings Gmbh

Inventors

• Groenewolt Matthijs
• Niemeier Manuela

Classifications

• B05D1/04

  involving the use of an electrostatic field {(B05D1/025 and B05D1/14 take precedence)} · CPC title

• B05D7/26

  synthetic lacquers or varnishes (B05D7/08, B05D7/16 take precedence) · CPC title

• C08G18/6254

  Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups · CPC title

• C09D175/12

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title

• C09D133/14 Primary

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title