Use of 2-(2-hydroxyphenyl)benzotriazole compounds as an UV absorbing agent in coatings

Patent metadata

Field	Value
Publication number	US-10119039-B2
Application number	US-201415026085-A
Country	US
Kind code	B2
Filing date	Oct 23, 2014
Priority date	Oct 29, 2013
Publication date	Nov 6, 2018
Grant date	Nov 6, 2018

Abstract

The present invention relates the use of a 2-(2-hydroxyphenyl)benzotriazole compound of the formula R(QUV) n as an UV absorbing agent in coatings.

First claim

The invention claimed is:

1. A method of stabilizing a coating composition comprising a film-forming binder, wherein the coating composition is selected from lacquers, paints for wood, ceramic materials, metals, plastics, or articles coated or stained with organic material, and radiation curable coating compositions, against the effect of light, comprising adding a 2-(2-hydroxyphenyl)benzotriazole compound of formula I
R(QUV) m   (I)

wherein
UV is a group of formula II

wherein
R1 is H, C 1 -C 20 alkyl, C 1 -C 5 alkoxy, C 1 -C 5 alkoxycarbonyl, C 3 -C 7 cycloalkyl, or naphthyl;
R2 and R3 which may be the same or different are H, C 1 -C 20 alkyl, C 1 -C 5 alkoxy, C 1 -C 5 alkoxycarbonyl, C 3 -C 7 cycloalkyl, phenyl, naphthyl or phenyl-C 1 -C 5 alkyl;
R4, R5, R6 and R7 which may be the same or different are H, C 1 -C 5 alkyl, C 1 -C 5 alkoxy, or halogen;
R10 is H or C 1 -C 20 alkyl;
Q is O; and
m is 1 and R is selected from C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 3 -C 7 cycloalkyl which may be substituted with one, two or three substituents independently selected from C 1 -C 5 alkyl, halogen, hydroxy and C 1 -C 5 alkoxy; and -(AO) x —R22, wherein A is —C 2 H 4 —, —C 3 H 6 — or —C 4 H 8 —, R22 is H, C 1 -C 20 alkyl, or —CO—R24, wherein R24 is C 1 -C 20 alkyl, and x is 1-20; or
m is 2 and R is C 1 -C 20 alkylene, C 2 -C 20 alkenylene, C 3 -C 7 cycloalkylene, or -(AO) x -A-, wherein A is —C 2 H 4 —, —C 3 H 6 — or —C 4 H 8 and x is 1-20;

to the coating composition.

2. The method according to claim 1 , wherein R1 is C 1 -C 8 alkyl and R2 and R3 are H or halogen.

3. The method according to claim 1 , wherein R4, R5, R6 and R7 are H or halogen.

4. The method according to claim 3 , wherein
R4, R5, R6 and R7 are H; or
R4 and R7 are H and R5 and R6 are halogen.

5. The method according to claim 1 , wherein in formula I m is 1 and R is C 1 -C 20 alkyl; or m is 2 and R is C 1 -C 20 alkylene or -(AO) x -A—.

6. The method according to claim 1 , further comprising adding a HALS compound to the coating composition.

7. The method according to claim 6 , wherein the HALS compound is at least one selected from the group consisting of bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidyl) n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, the condensate of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, linear or cyclic condensates of N,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine, tris(2,2,6,6-tetramethyl-4-piperidyl)nitrilotriacetate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, 1,1′-(1,2-ethanediyl)-bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, bis(1,2,2,6,6-pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate, 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione, bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)succinate, linear or cyclic condensates of N,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, the condensate of 2-chloro-4,6-bis(4-n-butylamino-2,2,6,6-tetramethylpiperidyl)-1,3,5-triazine and 1,2-bis(3-aminopropylamino)ethane, the condensate of 2-chloro-4,6-di-(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl)-1,3,5-triazine and 1,2-bis(3-aminopropylamino)ethane, 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione, 3-dodecyl-1-(2,2,6,6-tetramethyl-4-piperidyl)pyrrolidine-2,5-dione, 3-dodecyl-1-(1,2,2,6,6-pentamethyl-4-piperidyl)pyrrolidine-2,5-dione, a mixture of 4-hexadecyloxy- and 4-stearyloxy-2,2,6,6-tetramethylpiperidine, a condensate of N,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine, a condensate of 1,2-bis(3-aminopropylamino)ethane and 2,4,6-trichloro-1,3,5-triazine as well as 4-butylamino-2,2,6,6-tetramethylpiperidine; a condensate of 1,6-hexanediamine and 2,4,6-trichloro-1,3,5-triazine as well as N,N-dibutylamine and 4-butylamino-2,2,6,6-tetramethylpiperidine; N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylsuccinimide, N-(1,2,2,6,6-pentamethyl-4-piperidyl)-n-dodecylsuccinimide, 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro[4,5]decane, a reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro-[4,5]decane and epichlorohydrin, 1,1-bis(1,2,2,6,6-pentamethyl-4-piperidyloxycarbonyl)-2-(4-methoxyphenyl)ethene, N,N′-bis-formyl-N,N′-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine, a diester of 4-methoxymethylenemalonic acid with 1,2,2,6,6-pentamethyl-4-hydroxypiperidine, poly[methylpropyl-3-oxy-4-(2,2,6,6-tetramethyl-4-piperidyl)]siloxane, a reaction product of maleic acid anhydride-α-olefin copolymer with 2,2,6,6-tetramethyl-4-aminopiperidine or 1,2,2,6,6-pentamethyl-4-aminopiperidine, 2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine-4-yl)-N-butylamino]-6-(2-hydroxyethy)amino-1,3,5-triazine, 1-(2-hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine, 5-(2-ethylhexanoyl)oxymethyl-3,3,5-trimethyl-2-morpholinone, Sanduvor, 5-(2-ethylhexanoyl) oxymethyl-3,3,5-trimethyl-2-morpholinone, the reaction product of 2,4-bis[(1-cyclohexyloxy-2,2,6,6-piperidine-4-yl)butylamino]-6-chloro-s-triazine with N,N′-bis(3-aminopropyl)ethylenediamine), 1,3,5-tris(N-cyclohexyl-N-(2,2,6,6-tetramethylpiperazine-3-one-4-yl)amino)-s-triazine, and 1,3,5-tris(N-cyclohexyl-N-(1,2,2,6,6-pentamethylpiperazine-3-one-4-yl)amino)-s-triazine.

8. The method according to claim 1 , wherein in formula I m is 1 and R is a mixture of different C 1 -C 20 alkyl groups which is such that the compound of formula I is liquid at ambient temperature, C 2 -C 20 alkenyl, C 3 -C 7 cycloalkyl which may be substituted with one, two or three substituents independently selected from C 1 -C 5 alkyl, halogen, hydroxyl and C 1 -C 5 alkoxy; and -(AO) x —R22, wherein A is —C 2 H 4 —, —C 3 H 6 — or —C 4 H 8 —, R22 is H, C 1 -C 20 alkyl, or —CO—R24, wherein R24 is C 1 -C 20 alkyl, and x is 1-20.

Assignees

• Basf Se

Inventors

• Ehlis Thomas
• Braig Adalbert
• Peter Wolfgang
• Hainz Ruediger

Classifications

• C08G18/6225

  Polymers of esters of acrylic or methacrylic acid · CPC title

• C09D7/63 Primary

  organic · CPC title

• C08K5/34926

  also containing heterocyclic groups other than triazine groups · CPC title

• C08K5/3435 Primary

  Piperidines · CPC title

• C09D175/04

  Polyurethanes · CPC title