Novel light stabilizers

Patent metadata

Field	Value
Publication number	US-2016168356-A1
Application number	US-201414903645-A
Country	US
Kind code	A1
Filing date	Jul 3, 2014
Priority date	Jul 8, 2013
Publication date	Jun 16, 2016
Grant date	—

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

1 .- 18 . (canceled)

19 . 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;
C 3 -C 7 cycloalkyl;
—CH 2 —R 5 , wherein R 5 is acyclic C 2 -C 20 hydrocarbyl having one, two, or three double bonds;
C 1 -C 21 alkyl substituted with at least one substituent selected from C 1 -C 4 alkoxy, —OH or —CN;
C 3 -C 7 cycloalkyl substituted with at least one substituent selected from C 1 -C 4 alkyl, C 1 -C 4 alkoxy, —OH or —CN; or
C 4 -C 21 alkyl substituted with —CO—R 4 , wherein R 4 is C 1 -C 4 alkyl;

R 2 is H or C 1 -C 3 alkyl; and
R 3 is H or C 1 -C 4 alkyl.

20 . The compound according to claim 19 , wherein each R 1 is C 1 -C 21 alkyl and C 3 -C 7 cycloalkyl.

21 . The compound according to claim 19 , wherein each R 1 is C 1 -C 17 alkyl or C 3 -C 12 alkyl or C 3 -C 6 cycloalkyl.

22 . The compound according to claim 19 , 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.

23 . The compound according to claim 19 , 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.

24 . The compound according to claim 19 , wherein R 2 is H.

25 . The compound according to claim 19 , wherein A is —CH 2 —CH 2 —, —CH(CH 3 )—CH 2 —, or —CH 2 —CH(CH 3 )—.

26 . The compound according to claim 19 , wherein the compound is

27 . A composition comprising the compound according to claim 19 and an organic material.

28 . The composition according to claim 27 , in the form of a coating composition.

29 . The composition according to claim 27 , wherein the organic material is a polyethylene or polypropylene or polyurethane or styrenic polymer or a polyvinylchloride.

30 . The composition according to claim 27 , 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.

31 . The composition according to claim 27 , which further comprises a sterically hindered amine compound.

32 . The composition according to claim 27 , which further comprises one or more of the following compounds:
Bis-(1-octyloxy-2,2,6,6-tetramethyl-4-piperidinyl)sebacate (Tinuvin®123); condensate of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid dimethylester (Tinuvin®622); 2,2′-methylenebis(6-(2H-benzotriazol-2-yl)-4-1,1,3,3-tetramethylbutyl)phenol (Tinuvin®360); 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methylphenol (Tinuvin®571); 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol (Tinuvin®234); 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (Irganox®3114); tris(2,4-di-tert-butylphenyl)phosphite (Irgafos® 168); ethylenebis(oxyethylene)bis-(3-(5-tert-butyl-4-hydroxy-m-tolyl)-propionate) (Irganox®245); reaction product of methyl 3-(3-(2H-benzotriazole-2-yl)-5-t-butyl-4-hydroxyphenyl)propionate/polyethyleneglykol 300 (Tinuvin®213); 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 (Tinuvin®384-2); pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] (Irganox® 1010); Bis[2,4-di-tert-butylphenyl] pentaerythritol diphosphate (Irgafos®126); 2-(2H-benzotriazol-2-yl)-4,6-bis(1,1-dimethylpropyl)phenol (Tinuvin®PA 328); Reaction product of methyl 3-(3-(2H-benzotriazole-2-yl)-5-t-butyl-4-hydroxyphenyl)propionate/polyethyleneglykol 300 (Tinuvin®213); or a compound of the formula (Chimassorb® 2020)

33 . A coated article which is coated with the composition according to claim 27 .
A coated article which is coated with a composition comprising the compound according to claim 19 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 c) a clear coat that is in direct contact with the pigmented base coat and comprises a compound of claim 19 .

34 . A light stabilizer comprising the compound according to claim 19 .

35 . A process for preparing a coating on a substrate which comprises coating the substrate with the compound according to claim 19 .

36 . The process according to claim 35 , wherein the substrate is a metal, metal alloy, woods, plastic, ceramic or another coating.

Assignees

• Basf Se

Inventors

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

Classifications

• C08K5/3435 Primary

  Piperidines · CPC title

• C09D127/06

  Homopolymers or copolymers of vinyl chloride · CPC title

• C09D123/06

  Polyethylene · CPC title

• C07D211/46 Primary

  having a hydrogen atom as the second substituent in position 4 · CPC title

• C09D155/02

  ABS [Acrylonitrile-Butadiene-Styrene] polymers · CPC title