# US 5,707,690 A · Protective coating for wood

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- Number: US 5,707,690 A
- Document ID: US5707690A
- Status: Granted
- Kind: A
- Application number: 08/384,188
- Filed: 1995-02-06
- Granted: 1998-01-13
- Earliest claimed: 1994-02-10
- Assignees: Ciba-Geigy Corporation
- Inventors: Andreas Valet; Roger Meuwly
- Web page: https://patentgrep.com/patent/US5707690A

## CPC

- C07C 45/46: Friedel-Crafts reactions
- C07C 45/69: by addition to carbon-to-carbon double or triple bonds
- C07C 45/71: being hydroxy groups
- C07C 49/83: polycyclic
- C07C 49/84: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups
- C07C 323/22: containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07F 7/081: {comprising at least one atom selected from the elements N, O, halogen, S, Se or Te}
- C07F 7/0838: {Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21)}
- C09D 7/48: Stabilisers against degradation by oxygen, light or heat
- C08K 5/07: Aldehydes; Ketones
- C08K 5/132: Phenols containing keto groups {, e.g. benzophenones}
- Y10T 428/31989: Of wood
- Y10T 428/662: Wood timber product [e.g., piling, post, veneer, etc.]
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- 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)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The invention relates to a method of protecting surfaces of wood against damage by light by treatment with a coating composition comprising a benzophenone of the formula I ##STR1## in which the substituents are defined as in claim 1.

## Claims

### Claim 1

A method of protecting a surface of wood against damage by light by treatment with a coating composition comprising a benzophenone of the formula I ##STR18## in which i is a number from one to four;
L if i is one is H, C.sub.1 -C.sub.20 alkyl, c.sub.2 -c.sub.20 alkyl which is substituted by one or two --OH, by carboxyl, by C.sub.1 -C.sub.12 alkoxy, by phenoxy, by C.sub.2 -C.sub.20 alkylcarbonyl, by C.sub.3 -C.sub.20 alkenylcarbonyl, by C.sub.2 -C.sub.20 alkanoyloxy, by C.sub.3 -C.sub.20 alkenoyloxy or by phenyl, glycidyl, C.sub.4 -C.sub.20 alkyl which is interrupted by one to six O atoms or by one or two carbonyloxy or oxycarbonyl groups, C.sub.2 -C.sub.18 alkenyl, C.sub.2 -C.sub.18 alkanoyl, C.sub.3 -C.sub.18 alkenoyl, benzoyl, benzoyl which is substituted by one or two C.sub.1 -C.sub.4 alkyl groups, substituted or unsubstituted phenyl or naphthyl, or a group of the formula II, III, IV, V or VI:
--(CH.sub.2).sub.j --CH(OH)--(CH.sub.2).sub.k --O--R.sub.9 (II) where j,k=0-4;
--(CH.sub.2).sub.m --COOR.sub.9 (III) where m=1-4;
in which R.sub.9 is C.sub.1 -C.sub.18 alkyl or phenyl; ##STR19## in which a=0-50, b=0-50 and c=0-50; A is R.sub.7 or --O--Si(R.sub.7).sub.3 ;
E.sub.1 is OH, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy, cyclohexyl, phenyl or --O--Si(R.sub.7).sub.3 ;
E.sub.2 is H, C.sub.1 -C.sub.12 alkyl, cyclohexyl, phenyl, --Si(R.sub.7).sub.3 or --Si(R.sub.6)(R.sub.7).sub.2 ;
in which E.sub.1 and E.sub.2 together may also be a direct bond;
L.sub.1 is a direct bond or a divalent group of the formula --C.sub.n H.sub.2n --, --(CH.sub.2).sub.n --O--,
--CH.sub.2 CH(OH)CH.sub.2 --O-- --CH.sub.2 CH(OH)CH.sub.2 --O--(CH.sub.2).sub.3 --, where n=1-4;
R.sub.6 is a radical of the formula ##STR20## R.sub.7 is C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy, cyclohexyl or phenyl; and
R.sub.8 is C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.5 -C.sub.7 cycloalkyl or phenyl; ##STR21## in which x is 0, 1 or 2; R.sub.1 is C.sub.1 -C.sub.12 alkyl or C.sub.5 -C.sub.8 cycloalkyl; and
R.sub.1 ' is secondary or tertiary C.sub.3 -C.sub.12 alkyl or C.sub.5 -C.sub.8 cycloalkyl; ##STR22## in which L.sub.2 is as defined for L if i is two; and R.sub.3 ' is H or C.sub.1 -C.sub.18 alkyl;
L if i is two is C.sub.1 -C.sub.12 alkylene, C.sub.3 -C.sub.12 alkylene which is substituted by --OH, by C.sub.1 -C.sub.8 alkoxy, by C.sub.2 -C.sub.20 alkoxycarbonyl, by C.sub.2 -C.sub.20 alkanoyloxy, by C.sub.3 -C.sub.20 alkenoyloxy or by a silyl group of the formula (IV), C.sub.4 -C.sub.20 alkylene which is interrupted by one to six O atoms or by one or two carbonyloxy or oxycarbonyl groups, o-xylylene, m-xylylene, p-xylylene, isophthaloyl, phthaloyl, terephthaloyl or .alpha., .omega.-C.sub.4 -C.sub.12 alkanedioyl;
L if i is three is C.sub.3 -C.sub.12 alkanetriyl, C.sub.3 -C.sub.12 alkanetrioyl, trimellitoyl or C.sub.6 -.sub.20 alkanetriyl which is interrupted by three carbonyloxy or oxycarbonyl groups;
L if i is four is C.sub.4 -C.sub.16 alkanetetrayl, C.sub.4 -C.sub.16 alkanetetroyl, pyromellitoyl or C.sub.8 -C.sub.24 alkanetetrayl which is interrupted by four carbonyloxy or oxycarbonyl groups;
R.sub.2 is H, C.sub.1 -C.sub.18 alkyl or Cl;
R.sub.3 is H, Cl, --SR.sub.10, --SOR.sub.10 or --SO.sub.2 R.sub.10 ;
R.sub.4 is H, --OH, C.sub.1 -C.sub.18 alkyl or C.sub.2 -C.sub.18 alkenyl;
R.sub.5 is H, --OL, where L is as defined for if i is one, or C.sub.1 ; and
R.sub.10 is C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkyl which is substituted by --OH, by C.sub.1 -C.sub.12 alkoxy, by a silyl group of the formula (IV), by C.sub.2 -C.sub.12 alkanoyloxy, by C.sub.3 -C.sub.12 alkenoyloxy or by halogen, C.sub.3 -C.sub.18 alkenyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.7 -C.sub.15 phenylalkyl, C.sub.6 -C.sub.10 aryl, C.sub.6 -C.sub.10 aryl which is substituted by one or two C.sub.1 -C.sub.4 alkyl groups, or 1,1,2,2-tetrahydroperfluoro-C.sub.6 -C.sub.16 alkyl;
under the condition that, if i is one, at least one of the radicals R.sub.2, R.sub.3 and R.sub.5 is other than H.

### Claim 2 (depends on 1)

A method according to claim 1, wherein the benzophenone is of the formula I in which
i is one;
L is H, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.12 alkenyl, phenyl, naphthyl or a radical of the formula II, III or IV:
--(CH.sub.2).sub.j --CH(OH)--(CH.sub.2).sub.k --O--R.sub.9 (lI) where j,k=0-4;
--(CH.sub.2).sub.m -COOR.sub.9 (III) where m=1-4;
in which R.sub.9 is C.sub.1 -C.sub.18 alkyl or phenyl; ##STR23## in which a=1-50, b=0 and c=0-50; A is R.sub.7 or --O--Si(R.sub.7).sub.3 ;
E.sub.1 is OH, C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy, cyclohexyl, phenyl or --O--Si(R.sub.7).sub.3 ;
E.sub.2 is H, C.sub.1 -C.sub.12 alkyl, cyclohexyl, phenyl, --SiR.sub.6 (R.sub.7).sub.2 or --Si(R.sub.7).sub.3 ;
in which E.sub.1 and E.sub.2 together may also be a direct bond;
L.sub.1 is a direct bond or a divalent group of the formula --C.sub.n H.sub.2n --, --(CH.sub.2).sub.n --O-- or
--CH.sub.2 CH(OH)CH.sub.2 --O--(CH.sub.2).sub.3 --, where n=1-4;
R.sub.6 is a radical of the formula ##STR24## R.sub.7 is C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy, cyclohexyl or phenyl; and
R.sub.8 is C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.5 -C.sub.7 cycloalkyl or phenyl;
R.sub.2 is C.sub.1 -C.sub.12 alkyl or Cl or, if R.sub.5 is --OL or Cl, is H;
R.sub.3 is Cl or, if R.sub.2 or R.sub.5 is other than H, is H;
R.sub.4 is H, C.sub.1 -C.sub.12 alkyl or C.sub.2 -C.sub.12 alkenyl; and
R.sub.5 is H, --OL or Cl.

### Claim 3 (depends on 1)

A method according to claim 1, wherein the benzophenone is of the formula I in which
A)
i is one;
L is --CH.sub.2 --CH(OH)--CH.sub.2 --O--R.sub.9 (II);
R.sub.2 is C.sub.1 -C.sub.12 alkyl;
R.sub.3, R.sub.4 and R.sub.5 are H; and
R.sub.9 is C.sub.1 -C.sub.18 alkyl;
or
B)
i is one;
L is C.sub.1 -C.sub.12 alkyl;
R.sub.2 is C.sub.1 -C.sub.12 alkyl; and
R.sub.3, R.sub.4 and R.sub.5 are H;
or
C)
i is one;
L is C.sub.1 -C.sub.12 alkyl;
R.sub.2 is C.sub.1 -C.sub.12 alkyl;
R.sub.3 is Cl; and
R.sub.4 and R.sub.5 are H;
or
D)
i is one;
L is --(CH).sub.m --COOR.sub.9 (III) where m=1-4;
R.sub.2 is C.sub.1 -C.sub.12 alkyl;
R.sub.3, R.sub.4 and R.sub.5 are H; and
R.sub.9 is C.sub.1 -C.sub.18 alkyl;
or
E)
i is one;
L is C.sub.1 -C.sub.12 alkyl;
R.sub.2, R.sub.4 and R.sub.5 are H;
R.sub.3 is --SR.sub.10 or --SO.sub.2 R.sub.10 ; and
R.sub.10 is C.sub.1 -C.sub.12 alkyl or phenyl.

### Claim 4 (depends on 1)

A method according to claim 1, wherein the coating composition comprising a compound of the formula (I) is a topcoat.

### Claim 5 (depends on 1)

A method according to claim 1, wherein the coating composition comprising a compound of the formula (I) is a topcoat which is a clearcoat.

### Claim 6 (depends on 1)

A method according to claim 1, wherein the coating composition comprising a compound of the formula (I) is a topcoat which contains a binder based on an alkyd resin.

### Claim 7 (depends on 1)

A method according to claim 1, wherein the coating composition comprising a compound of the formula (I) is a topcoat which contains one or more further light stabilizers.

### Claim 8 (depends on 1)

A method according to claim 1, wherein the coating composition comprising a compound of the formula (I) is a topcoat which contains a sterically hindered amine as additional light stabilizer.

### Claim 9 (depends on 1)

A method according to claim 1, which comprises using a mixture comprising a benzophenone of the formula (I) in which R.sub.2 and R.sub.3 and R.sub.5 are hydrogen with a benzophenone of the formula (I) in which at least one of the radicals R.sub.2, R.sub.3 and R.sub.5 is not hydrogen.

### Claim 10 (depends on 1)

A method according to claim 1, wherein the coating composition comprising a compound of the formula (I) is a topcoat which contains as additional light stabilizer a compound from the series of the benzotdazoles and/or hydroxyphenyltriazines.