Light stabilizers

Patent metadata

Field	Value
Publication number	US-9969864-B2
Application number	US-201414903645-A
Country	US
Kind code	B2
Filing date	Jul 3, 2014
Priority date	Jul 8, 2013
Publication date	May 15, 2018
Grant date	May 15, 2018

Abstract

The present invention relates to symmetric diesters of hydroxyalkyl-4-hydroxy-tetraalkylpiperidine compounds and their use as light stabilizers. They are compatible with and soluble in coating formulations of different polarity.

First claim

The invention claimed is:

1. A compound having the formula (I)

wherein
A is —CH(R 3 )—CH 2 — or —CH 2 — CH(R 3 )—;
each R 1 is the same and is C 1 -C 21 alkyl or C 3 -C 7 cycloalkyl;
R 2 is H or C 1 -C 3 alkyl; and
R 3 is H or C 1 -C 4 alkyl.

2. The compound according to claim 1 , wherein each R 1 is C 1 -C 17 alkyl.

3. The compound according to claim 1 , wherein each R 1 is selected from C 1 , C 2 , C 3 , C 4 , C 5 , C 6 , C 7 , C 8 , C 9 , C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , and C 17 alkyl.

4. The compound according to claim 1 , wherein each R 1 is C 1 -C 21 alkyl substituted with at least one substituent selected from C 1 -C 4 alkoxy and —OH.

5. The compound according to claim 1 , wherein R 2 is H.

6. The compound according to claim 1 , wherein A is —CH 2 —CH 2 —, —CH(CH 3 )—CH 2 —, or —CH 2 —CH(CH 3 )—.

7. A compound of the formula

8. A composition comprising the compound according to claim 1 and an organic material.

9. The composition according to claim 8 , in the form of a coating composition.

10. The composition according to claim 8 , wherein the organic material is a polyethylene or polypropylene or polyurethane or styrenic polymer or a polyvinylchloride.

11. The composition according to claim 8 , which further comprises one or more UV absorbers of the hydroxy-phenyl-benzotriaziole or hydroxy-phenyl-triazine or hydroxyl-benzophenone or oxanilide class or cyanoacrylate or malonate and combinations thereof.

12. The composition according to claim 8 , which further comprises a sterically hindered amine compound.

13. The composition according to claim 8 , which further comprises one or more of the following compounds:
Bis-(1-octyloxy-2,2,6,6-tetramethyl-4-piperidinyl)sebacate;
condensate of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid dimethylester;
2,2′-methylenebis(6-(2H-benzotriazol-2-yl)-4-1,1,3,3-tetramethylbutyl)phenol;
2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methylphenol;
2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol;
1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione;
tris(2,4-di-tert-butylphenyl)phosphite;
ethylenebis(oxyethylene)bis-(3-(5-tert-butyl-4-hydroxy-m-tolyl)-propionate);
reaction product of methyl 3-(3-(2H-benzotriazole-2-yl)-5-t-butyl-4-hydroxyphenyl)propionate/polyethyleneglykol 300;
3-(2H-benzotriazol-2-yl)-5-(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid C 7 -C 9 alkylester, optionally in admixture with 1-methoxy-2-propyl acetate;
pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate];
Bis[2,4-di-tert-butylphenyl] pentaerythritol diphosphate;
2-(2H-benzotriazol-2-yl)-4,6-bis(1,1-dimethylpropyl)phenol;
Reaction product of methyl 3-(3-(2H-benzotriazole-2-yl)-5-t-butyl-4-hydroxyphenyl)propionate/polyethyleneglykol 300; or
a compound of the formula

 wherein n is a number such that the molecular weight is from 2600 to 3400 g/mol.

14. A coated article which is coated with the composition according to claim 8 .

15. A coated article which is coated with a composition comprising the compound according to claim 1 and an organic material comprising a metal substrate, and coat comprising
a) a primer coat which is electrodeposited onto the metal substrate;
b) at least one pigmented base coat which is in direct contact with the primer coat, and a clear coat that is in direct contact with the pigmented base coat and comprises a compound of claim 1 .

16. A light stabilizer comprising the compound according to claim 1 .

17. A process for preparing a coating on a substrate which comprises coating the substrate with the compound according to claim 1 .

18. The process according to claim 17 , wherein the substrate is a metal, metal alloy, woods, plastic, ceramic or another coating.

19. The compound according to claim 1 , wherein each R 1 is C 3 -C 12 alkyl.

20. The compound according to claim 1 , wherein each R 1 is C 3 -C 6 cycloalkyl.

Assignees

• Basf Se

Inventors

• Peter Wolfgang
• Braig Adalbert
• Berens Ulrich
• Schöning Kai-Uwe
• Grob Markus
• Tartarini Cinzia
• Weyland Tania

Classifications

• C09D123/12

  Polypropene · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C09D167/06

  Unsaturated polyesters having carbon-to-carbon unsaturation · CPC title

• C09D127/06

  Homopolymers or copolymers of vinyl chloride · CPC title

• C08K5/3435 Primary

  Piperidines · CPC title