Special UV absorbers for curable UV-protective coatings
View Patent ↗The present invention relates to organic UV absorbers which have two or more polymerizable acrylate or methacrylate groups in the molecule, to coating compositions comprising such UV absorbers, and also to coatings produced therefrom and to substrates coated therewith.
1. A compound of the general formula (I)
A-X(-T) n (I),
wherein
A represents
wherein
Y 1 and Y 2 independently of one another represent substituents of the general formula
wherein
r represents 0 or 1,
R 1 , R 2 , R 3 independently of one another represent H, OH, C 1-20 -alkyl, C 4-12 -cycloalkyl, C 2-20 -alkenyl, C 1-20 -alkoxy, C 4-12 -cycloalkoxy, C 2-20 -alkenyloxy, C 7-20 -aralkyl, halogen, —C≡N, C 1-5 -haloalkyl, —SO 2 R′, —SO 3 H, —SO 3 M (M=alkali metal), —COOR′, —CONHR′, —CONR′R″, —OCOOR′, —OCOR′, —OCONHR′, (meth)acrylamino, (meth)acryloxy; C 6-12 -aryl optionally substituted by C 1-12 -alkyl, C 1-12 -alkoxy, CN and/or by halogen, or C 3-12 -heteroaryl optionally substituted by C 1-12 -alkyl, C 1-12 -alkoxy, CN and/or by halogen, wherein
M represents an alkali metal cation,
R′ and R″ represent H, C 1-20 -alkyl, C 4-12 -cycloalkyl; C 6-12 -aryl optionally substituted by C 1-12 -alkyl, C 1-12 -alkoxy, CN and/or by halogen, or C 3-12 -heteroaryl optionally substituted by C 1-12 -alkyl, C 1-12 -alkoxy, CN and/or by halogen,
X represents an optionally substituted linear or branched open-chain linker of carbon, oxygen, nitrogen, sulfur, phosphorus and/or silicon in the chain,
T represents an acrylate radical —O—(C═O)—CH═CH 2 or a methacrylate radical —O—(C═O)—C(CH 3 )═CH 2 , and
n represents an integer from 2 to 5.
2. The compound according to claim 1 , wherein the compound is of the general formula (I-1)
wherein
Z represents an optionally substituted linear or branched C 1-20 -alkylene radical or C 1-20 -alkylene ether radical.
3. The compound according to claim 1 , wherein in the substituents Y 1 and Y 2 , r in each case represents 1.
4. The compound according to claim 1 , wherein in the substituents Y 1 and Y 2 , the radicals R 1 , R 2 and R 3 in each case represent H.
5. The compound according to claim 1 , wherein the compound is of formulae from (I-1-1) to (I-1-12)
6. A coating composition comprising at least one compound according to claim 1 and at least one organic solvent.
7. The coating composition according to claim 6 , further comprising at least one initiator.
8. The coating composition according to claim 7 , wherein the at least one initiator is a photoinitiator.
9. The coating composition according to claim 6 , further comprising at least one stabilizer from the group of Hindered Amine Light Stabilizers (HALS).
10. The coating composition according to claim 6 , further comprising at least one reactive diluent or at least one oligomeric aliphatic urethane acrylate or polyester acrylate.
11. The coating composition according to claim 6 , further comprising one or more further additives selected from the group consisting of stabilizers, flow agents, surface additives, pigments, colorants, adhesion promoters, IR absorbers, and UV absorbers other than the compounds of the general formula (I).
12. A method of coating a substrate, comprising
A) applying the coating composition according to claim 6 to the substrate to form a layer,
B) removing at least part of the at least one organic solvent from the layer obtained according to step A), and
C) curing the layer.
13. A coating produced from the coating composition according to claim 6 .
14. An article, comprising at least one substrate and at least one coating produced from at least one coating composition according to claim 6 .
15. The article according to claim 14 , wherein the at least one substrate is a moulded article, an extrudate or a coextrudate comprising one or more thermoplastic plastics.
16. The article according to claim 14 , wherein the article is a film, a sheet, a multi-wall sheet, a headlamp cover plate, an automotive glazing or an architectural glazing.