Fluorine-containing nonaqueous coating material composition, coating methods, and the use of the coating material composition

Patent metadata

Field	Value
Publication number	US-9574089-B2
Application number	US-201314432609-A
Country	US
Kind code	B2
Filing date	Aug 16, 2013
Priority date	Oct 4, 2012
Publication date	Feb 21, 2017
Grant date	Feb 21, 2017

Abstract

Nonaqueous coating material compositions comprising at least one polyhydroxyl and (per)fluoroalkyl group-containing poly(meth)acrylate component (A), at least one polyisocyanate group-containing compounds (B), and one or more catalysts (D). Also provided are multistage coating methods using the coating material compositions, and also the use of the coating material compositions as a clearcoat material and for coating of wind energy systems or aircraft, or parts thereof, more particularly as an anti-icing coating.

First claim

The invention claimed is:

1. A nonaqueous coating material composition comprising:
(A) 30% to 80% by weight of a (per)fluoroalkyl group-containing poly(meth)acrylate component (A), wherein the poly(meth)acrylate component (A) contains multiple hydroxyl groups,
(B) 20% to 70% by weight of one or more polyisocyanate compounds (B), and
(D) one or more catalysts (D),
the weight percentages of components (A) and (B) being based in each case on the binder content of components (A) and (B), and the sum of the weight fractions of components (A) plus (B) being in each case 100% by weight,
wherein the poly(meth)acrylate component (A) comprises as a synthesis component 0.05% to 15.0% by weight, based in each case on the amount of all of the compounds used in preparing the poly(meth)acrylate component (A), of one or more (per)fluoroalkyl group-containing reaction products (U) of:
(i) one or more diisocyanates (PI) having two isocyanate groups with different reactivities,
(ii) one or more (per)fluoroalkyl monoalcohol components (FA), and
(iii) optionally one or more compounds (V) having at least one group (G1) that is reactive toward isocyanate groups, and optionally having a further functional group (G2), which is different from group (G1).

2. The coating material composition of claim 1 , wherein the one or more (per)fluoroalkyl monoalcohol components (FA) have the general formula (I):
CF 3 —(CF 2 ) x —(CH 2 ) y —O-A z -H  (I)

and/or of the general formula (II):
CR 1 3 —(CR 2 2 ) x —(CH 2 ) y —O-A z -H  (II)

in which R 1 and R 2 independently of one another are H, F, or CF 3 , but R 1 and R 2 must not simultaneously be H,
x is 1-20, y is 1-6, and z is 0-100,
A is CR′R″—CR′″R″″—O or (CR′R″) a —O or CO—(CR′R″) b —O,
R′, R″, R′″, and R″″ are independently of one another H, alkyl, cycloalkyl, aryl, or any organic radical having 1 to 25 C atoms, a and b are each 3-5, and A z is a homopolymer, copolymer or block polymer of any A.

3. The coating material composition of claim 1 , wherein the one or more (per)fluoroalkyl monoalcohol components (FA) have the general formula:
F(CF 2 CF 2 ) l —(CH 2 CH 2 O) m —H  (III)

and/or
CF 3 —(CF 2 ) n —(CH 2 ) o —O—H  (IV)

in which l is 1-8, m is 1 to 15, n is 1 to 12, and o is 1 to 10.

4. The coating material composition of claim 1 , wherein the poly(meth)acrylate component (A) comprises 0.1% to 10.0% by weight, based in each case on the amount of all of the compounds used in preparing the poly(meth)acrylate component (A), of the one or more (per)fluoroalkyl-containing reaction products (U).

5. The coating material composition of claim 1 , wherein the poly(meth)acrylate component (A) comprises, as the synthesis component, the (per)fluoroalkyl group-containing reaction product (U) of:
(i) one or more diisocyanates (PI) having two isocyanate groups with different reactivities,
(ii) one or more (per)fluoroalkyl monoalcohol components (FA), and
(iii) one or more compounds (V) having a group (G1) that is reactive toward isocyanate groups, and having an ethylenically unsaturated double bond (G2).

6. The coating material composition of claim 1 , wherein the poly(meth)acrylate component (A) comprises, as the synthesis component, the (per)fluoroalkyl group-containing reaction product (U) of:
(i) one or more aliphatic and/or cycloaliphatic diisocyanates (PI) having two isocyanate groups with different reactivities,
(ii) one or more (per)fluoroalkyl monoalcohol components (FA)
CF 3 —(CF 2 ) r —(CH 2 ) p —OH  (V)

 in which r is 1 to 8, and p is 1 to 6,
(iii) one or more compounds (V) having at least one of a carboxyl group and a hydroxyl group (G1), and having at least one of an acrylically unsaturated double bone and a methacrylically unsaturated double bond (G2).

7. The coating material composition of claim 1 , wherein the poly(meth)acrylate component (A) consists of
one or more saturated (per)fluoroalkyl group-containing polyacrylates, wherein the polyacrylates contain multiple hydroxyl groups; or one or more saturated (per)fluoroalkyl group-containing polymethacrylates, wherein the polymethacrylates contain multiple hydroxyl groups; or a mixture of one or more saturated (per)fluoroalkyl group-containing polyacrylates and one or more saturated (per)fluoroalkyl group-containing polymethacrylates, wherein the polyacrylates and polymethacrylates contain multiple hydroxyl groups.

8. The coating material composition of claim 1 , wherein the poly(meth)acrylate component (A) comprises, as the synthesis component, the (per)fluoroalkyl group-containing reaction product (U) of:
(i) 1 mol of one or more diisocyanates (PI) having two isocyanate groups with different reactivities,
(ii) 1 mol of one or more (per)fluoroalkyl monoalcohol components (FA), and
(iii) 1 mol of one or more ethylenically unsaturated compounds (V) having a group (G1) that is reactive toward isocyanate groups.

9. The coating material composition of claim 1 , wherein the poly(meth)acrylate component (A) is saturated and synthesized from:
(a1) 0.05% to 15.0% by weight of one or more (per)fluoroalkyl group-containing, ethylenically unsaturated reaction products (U),
(a2) 10% to 50% by weight of one or more hydroxyl group-containing monomers,
(a3) 10% to 89.95% by weight of one or more alkyl and/or cycloalkyl esters of ethylenically unsaturated carboxylic acids,
(a4) 0% to 50% by weight of one or more vinylaromatic compounds, and
(a5) 0% to 10% by weight of further ethylenically unsaturated monomers,
the sum of the weight fractions of the monomers (a1) to (a5) being in each case 100% by weight.

10. The coating material composition of claim 1 , wherein the poly(meth)acrylate component (A) has an OH number of 60 to 300 mg KOH/g.

11. The coating material composition of claim 1 , wherein the poly(meth)acrylate component (A) has a glass transition temperature of −100° C. to +100° C.

12. The coating material composition of claim 1 , wherein the coating material composition further comprises 0.2% to 15.0% by weight, based in each case on the binder fraction of the sum of the components (A) plus (B), of at least one aromatic carboxylic acid (S) whose carboxyl group is in conjugation with a π-electron system.

13. The coating material composition of claim 1 , wherein the poly(meth)acrylate component (A) comprises as synthesis component the (per)fluoroalkyl group-containing reaction product (U) of
(i) isophorone diisocyanate,
(ii) 2-(perfluorohexyl)ethanol, and
(iii) hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxyalkylcaprolactone acrylate, and/or hydroxyalkylcaprolactone methacrylate.

14. A method of coating comprising: applying to an optionally precoated substrate a layer of the coating material composition of claim 1 .

15. The method of coating of claim 14 , wherein the coating material composition, after being applied, is cured at temperatures between 20 and 80° C.

16. The method of coating of claim 14 , wherein the optionally precoated substrate is an aircraft or a wind energy system, or one or more parts thereof.

17. The method of coating of claim 14 , wherein the coating material composition is applied as an outermost coating film to rotor blades of wind energy systems.

18. The method of coating according to claim 14 , wherein a coating formed from the coating material composition is effective as a permanent water-repellent and soiling-repellent surface coating.

19. The method of coating according to claim 14 , wherein a coating formed from the coating material composition is ef

Assignees

• Basf Coatings Gmbh

Inventors

• Klein Günter
• Hoffmann Peter
• Feigl Andreas
• Niedermair Fabian
• Steidl Norbert
• Walther Burkhard

Classifications

• F03D1/06

  Rotors · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C08G18/672

  Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C08G18/6725

  containing ester groups other than acrylate or alkylacrylate ester groups · CPC title