# US 10,119,039 B2 · Use of 2-(2-hydroxyphenyl)benzotriazole compounds as an UV absorbing agent in coatings

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- Number: US 10,119,039 B2
- Document ID: US10119039B2
- Status: Granted
- Kind: B2
- Application number: 15/026,085
- Filed: 2014-10-23
- Published: 2016-07-28
- Granted: 2018-11-06
- Earliest claimed: 2013-10-29
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Thomas Ehlis; Adalbert Braig; Wolfgang Peter; Ruediger Hainz
- Web page: https://patentgrep.com/patent/US10119039B2

## CPC

- C09D 7/48: Stabilisers against degradation by oxygen, light or heat
- C07D 249/20: with aryl radicals directly attached in position 2
- C08G 18/6225: {Polymers of esters of acrylic or methacrylic acid}
- C08G 18/7831: {containing biuret groups}
- C08K 5/3435: Piperidines
- C08K 5/3475: condensed with carbocyclic rings
- C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16}
- C09D 5/00: Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes
- C09D 133/06: of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D 175/04: Polyurethanes
- C08K 5/34926: {also containing heterocyclic groups other than triazine groups}
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## 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.

## Claims

### Claim 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, C1-C20alkyl, C1-C5alkoxy, C1-C5alkoxycarbonyl, C3-C7cycloalkyl, or naphthyl;
R2 and R3 which may be the same or different are H, C1-C20alkyl, C1-C5alkoxy, C1-C5alkoxycarbonyl, C3-C7cycloalkyl, phenyl, naphthyl or phenyl-C1-C5alkyl;
R4, R5, R6 and R7 which may be the same or different are H, C1-C5alkyl, C1-C5alkoxy, or halogen;
R10 is H or C1-C20alkyl;
Q is O; and
m is 1 and R is selected from C1-C20alkyl, C2-C20alkenyl, C3-C7cycloalkyl which may be substituted with one, two or three substituents independently selected from C1-C5alkyl, halogen, hydroxy and C1-C5alkoxy; and -(AO)x—R22, wherein A is —C2H4—, —C3H6— or —C4H8—, R22 is H, C1-C20alkyl, or —CO—R24, wherein R24 is C1-C20alkyl, and x is 1-20; or
m is 2 and R is C1-C20alkylene, C2-C20alkenylene, C3-C7cycloalkylene, or -(AO)x-A-, wherein A is —C2H4—, —C3H6— or —C4H8 and x is 1-20;
to the coating composition.

### Claim 2 (depends on 1)

The method according to claim 1, wherein R1 is C1-C8alkyl and R2 and R3 are H or halogen.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 3)

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.

### Claim 5 (depends on 1)

The method according to claim 1, wherein in formula I m is 1 and R is C1-C20alkyl; or m is 2 and R is C1-C20alkylene or -(AO)x-A—.

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 6)

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.

### Claim 8 (depends on 1)

The method according to claim 1, wherein in formula I m is 1 and R is a mixture of different C1-C20alkyl groups which is such that the compound of formula I is liquid at ambient temperature, C2-C20alkenyl, C3-C7cycloalkyl which may be substituted with one, two or three substituents independently selected from C1-C5alkyl, halogen, hydroxyl and C1-C5alkoxy; and -(AO)x—R22, wherein A is —C2H4—, —C3H6— or —C4H8—, R22 is H, C1-C20alkyl, or —CO—R24, wherein R24 is C1-C20alkyl, and x is 1-20.