US5106891A
Expired / Lapsed
US
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Light stabilized coating compositions containing a mixture of 2-hydroxyphenylbenzotriazole and 2-hydroxyphenyltriazine
Assignee: BASF Corp
•
Filing: 1991-03-22
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Granted: 1992-04-21
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Expires: 2011-03-22
Abstract
Abstract Coating compositions which, in addition to a 2-hydroxyphenylbenzotriazole UV absorber, also contain a UV absorber belonging to the group of the 2-hydroxyphenyltriazines, 2-hydroxybenzophenones and/or, in addition to a 2-hydroxyphenyltriazine, also contain a 2-hydroxybenzophenone and/or oxanilide are described.
Inventors
- 👤 Andreas Valet
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 18:54
CPC Classifications
C; C09; C09K; C09K3/00; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3477; C08K5/3492; C08K5/04; C08K5/13; C08K5/132; C08K5/20; C08K5/3472; C08K5/3475; C09D; C09D7/00; C09D7/40; C09D7/48; C08K5/0008; C08K5/005; C08K5/07
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
791 words
A coating composition which contains, as the UV absorber, a mixture of at least one 2-hydroxyphenylbenzotriazole and at least one 2-hydroxyphenyltriazine, wherein the 2-hydroxyphenylbenzotriazole has the formula 1a or 1b ##STR39## in which in formula 1a or 1b R 1 is hydrogen, alkyl having 1 to 24 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, R 2 is hydrogen, halogen, alkyl having 1 to 18 carbon atoms or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, and R 3 is hydrogen, chlorine or alkyl having 1 to 4 carbon atoms; with at least one of the radicals R 1 and R 2 being other than hydrogen; T is hydrogen or alkyl having 1 to 6 carbon atoms, T 1 is hydrogen, chlorine or alkyl having 1 to 4 carbon atoms, n is 1 or 2, when n is 1, T 2 is chlorine or a radical of the formula--OT 3 , wherein T 3 is hydrogen, alkyl which has 1 to 18 carbon atoms and is unsubstituted or substituted by 1 to 3 hydroxyl groups; alkyl of 3 to 18 carbon atoms interrupted once or several times by --O-- and is unsubstituted or substituted by hydroxyl; alkenyl which has 2 to 18 carbon atoms and is unsubstituted or substituted by hydroxyl; phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or a radical of the formula --CH 2 CH(OH)--T 7 or glycidyl; where T 7 is hydrogen, alkyl having 1 to 18 carbon atoms or phenyl, and when n is 2, T 2 is a radical of the formula --O--T 9 --O--, wherein T 9 is alkylene having 2 to 8 carbon atoms, alkenylene having 4 to 8 carbon atoms, cyclohexylene, alkylene which has 2 to 8 carbon atoms and is interrupted once or several times by --O--; and in which in formula 2 u is 1 or 2 r is an integer from 1 to 3 the substituents Y 1 independently of one another are hydrogen, hydroxyl, halogenomethyl, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 18 carbon atoms or halogen, when u is 1, Y 2 is alkyl having 1 to 18 carbon atoms, alkyl which has 1 to 12 carbon atoms and is substituted by --COOH, --COOY 8 , --CONH 2 , --CONHY 9 , --CONY 9 Y 10 , --CN, --OCOY 11 or mixtures thereof; alkyl which has 4 to 20 carbon atoms which is interrupted by one or more oxygen atoms and is unsubstituted or substituted by hydroxyl or alkoxy having 1 to 12 carbon atoms; alkenyl having 3 to 6 carbon atoms, glycidyl, phenylalkyl which has 1 to 5 carbon atoms in the alkyl moiety and is unsubstituted or substituted by hydroxyl, chlorine and/or methyl; --COY 12 or --SO 2 Y 13 , wherein Y 8 is alkyl having 1 to 18 carbon atoms, alkenyl having 3 to 18 carbon atoms, alkyl which has 3 to 20 carbon atoms and is interrupted by one or more oxygen atoms or said alkyl substituted by hydroxyl; alkenyl having 3 to 18 carbon atoms, glycidyl or phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety, Y 9 and Y 10 independently of one another are alkyl having 1 to 12 carbon atoms, alkoxyalkyl having 3 to 12 carbon atoms, dialkylaminoalkyl having 4 to 16 carbon atoms or cycloalkyl having 5 to 12 carbon atoms, Y 11 is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms or phenyl, Y 12 is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms, phenyl, alkoxy having 1 to 12 carbon atoms, phenoxy, alkylamino having 1 to 12 carbon atoms or phenylamino, and Y 13 is alkyl having 1 to 18 carbon atoms, phenyl or alkylphenyl having 1 to 8 carbon atoms in the alkyl radical; and when u is 2, Y 2 is alkylene having 2 to 16 carbon atoms, alkenylene having 4 to 12 carbon atoms, xylylene, alkylene which has 3 to 20 carbon atoms and is interrupted by one or more --O-- atoms and/or is substituted by hydroxyl; --CH 2 CH(OH)CH 2 --O--Y 15 --OCH 2 CH(OH)CH 2 -- or --(CH 2 ) m --CO 2 --Y 18 --OCO--(CH 2 ) m --, in which m is 1, 2 or 3, wherein Y 15 is alkylene having 2 to 10 carbon atoms, phenylene or a group phenylene-M-phenylene in which M is --O--, --S--, --SO 2 --, --CH 2 -- or --C(CH 3 ) 2 --, and Y 18 is alkylene having 2 to 10 carbon atoms or alkylene which has 4 to 20 carbon atoms and is interrupted once or several times by oxygen.
Claim 2
Dependent Claim
791 words
A coating composition which contains, as the UV absorber, a mixture of at least one 2-hydroxyphenylbenzotriazole and at least one 2-hydroxyphenyltriazine, wherein the 2-hydroxyphenylbenzotriazole has the formula 1a or 1b ##STR39## in which in formula 1a or 1b R 1 is hydrogen, alkyl having 1 to 24 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, R 2 is hydrogen, halogen, alkyl having 1 to 18 carbon atoms or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, and R 3 is hydrogen, chlorine or alkyl having 1 to 4 carbon atoms; with at least one of the radicals R 1 and R 2 being other than hydrogen; T is hydrogen or alkyl having 1 to 6 carbon atoms, T 1 is hydrogen, chlorine or alkyl having 1 to 4 carbon atoms, n is 1 or 2, when n is 1, T 2 is chlorine or a radical of the formula--OT 3 , wherein T 3 is hydrogen, alkyl which has 1 to 18 carbon atoms and is unsubstituted or substituted by 1 to 3 hydroxyl groups; alkyl of 3 to 18 carbon atoms interrupted once or several times by --O-- and is unsubstituted or substituted by hydroxyl; alkenyl which has 2 to 18 carbon atoms and is unsubstituted or substituted by hydroxyl; phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or a radical of the formula --CH 2 CH(OH)--T 7 or glycidyl; where T 7 is hydrogen, alkyl having 1 to 18 carbon atoms or phenyl, and when n is 2, T 2 is a radical of the formula --O--T 9 --O--, wherein T 9 is alkylene having 2 to 8 carbon atoms, alkenylene having 4 to 8 carbon atoms, cyclohexylene, alkylene which has 2 to 8 carbon atoms and is interrupted once or several times by --O--; and in which in formula 2 u is 1 or 2 r is an integer from 1 to 3 the substituents Y 1 independently of one another are hydrogen, hydroxyl, halogenomethyl, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 18 carbon atoms or halogen, when u is 1, Y 2 is alkyl having 1 to 18 carbon atoms, alkyl which has 1 to 12 carbon atoms and is substituted by --COOH, --COOY 8 , --CONH 2 , --CONHY 9 , --CONY 9 Y 10 , --CN, --OCOY 11 or mixtures thereof; alkyl which has 4 to 20 carbon atoms which is interrupted by one or more oxygen atoms and is unsubstituted or substituted by hydroxyl or alkoxy having 1 to 12 carbon atoms; alkenyl having 3 to 6 carbon atoms, glycidyl, phenylalkyl which has 1 to 5 carbon atoms in the alkyl moiety and is unsubstituted or substituted by hydroxyl, chlorine and/or methyl; --COY 12 or --SO 2 Y 13 , wherein Y 8 is alkyl having 1 to 18 carbon atoms, alkenyl having 3 to 18 carbon atoms, alkyl which has 3 to 20 carbon atoms and is interrupted by one or more oxygen atoms or said alkyl substituted by hydroxyl; alkenyl having 3 to 18 carbon atoms, glycidyl or phenylalkyl having 1 to 5 carbon atoms in the alkyl moiety, Y 9 and Y 10 independently of one another are alkyl having 1 to 12 carbon atoms, alkoxyalkyl having 3 to 12 carbon atoms, dialkylaminoalkyl having 4 to 16 carbon atoms or cycloalkyl having 5 to 12 carbon atoms, Y 11 is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms or phenyl, Y 12 is alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 18 carbon atoms, phenyl, alkoxy having 1 to 12 carbon atoms, phenoxy, alkylamino having 1 to 12 carbon atoms or phenylamino, and Y 13 is alkyl having 1 to 18 carbon atoms, phenyl or alkylphenyl having 1 to 8 carbon atoms in the alkyl radical; and when u is 2, Y 2 is alkylene having 2 to 16 carbon atoms, alkenylene having 4 to 12 carbon atoms, xylylene, alkylene which has 3 to 20 carbon atoms and is interrupted by one or more --O-- atoms and/or is substituted by hydroxyl; --CH 2 CH(OH)CH 2 --O--Y 15 --OCH 2 CH(OH)CH 2 -- or --(CH 2 ) m --CO 2 --Y 18 --OCO--(CH 2 ) m --, in which m is 1, 2 or 3, wherein Y 15 is alkylene having 2 to 10 carbon atoms, phenylene or a group phenylene-M-phenylene in which M is --O--, --S--, --SO 2 --, --CH 2 -- or --C(CH 3 ) 2 --, and Y 18 is alkylene having 2 to 10 carbon atoms or alkylene which has 4 to 20 carbon atoms and is interrupted once or several times by oxygen.
Claim 3
Dependent Claim
25 words
A coating composition according to claim 1, wherein, in the mixture, the 2-hydroxy-phenylbenzotriazole is present in a weight ratio of 3:1 to 1:3, to 2-hydroxyphenyltriazine.
Claim 4
Dependent Claim
18 words
A composition according to claim 2 wherein the weight ratio of 2-hydroxyphenylbenzotriazole to 2-hydroxyphenyltriazine is 2:1 to 1:2.
Claim 5
Dependent Claim
34 words
A coating composition according to claim 1, wherein the substituent R 1 or R 2 in the compounds of the formula (1a) is located in the ortho-position or para-position relative to the hydroxyl group.
Claim 6
Dependent Claim
65 words
A coating composition according to claim 1, in which, in the compounds of the formula (1a), R 1 is hydrogen or alkyl having 1 to 20 carbon atoms, R 2 is hydrogen, alkyl having 1 to 18 carbon atoms or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety and R 3 is hydrogen, chlorine or alkyl having 1 to 4 carbon atoms.
Claim 7
Dependent Claim
60 words
A coating composition according to claim 5, in which R 1 is in the ortho-position relative to the hydroxyl group and is hydrogen or alkyl having 4 to 12 carbon atoms, R 2 is in the para-position relative to the hydroxyl group and is alkyl having 1 to 6 carbon atoms or cumyl and R 3 is hydrogen or chlorine.
Claim 8
Dependent Claim
34 words
A coating composition according to claim 6, in which R 1 is alkyl having 8 to 12 carbon atoms, R 2 is alkyl having 4 to 6 carbon atoms and R 3 is hydrogen.
Claim 9
Dependent Claim
143 words
A coating composition according to claim 1, in which, in the compounds of the formula (1b), T is alkyl having 1 to 6 carbon atoms, T 1 is hydrogen, chlorine or alkyl having 1 to 4 carbon atoms, n is 1 or 2 and, when n is 1, T 2 is one of the radicals of the formula --OT 3 and, when n is 2, T 2 is a radical of the formula --O--T 9 --O-- in which T 3 is hydrogen, alkyl having 1 to 18 carbon atoms or alkyl which has 3 to 18 carbon atoms and is interrupted once or several times by --O--, and T 9 is alkylene having 2 to 8 carbon atoms, alkenylene having 4 to 8 carbon atoms or alkylene which has 2 to 18 carbon atoms and is interrupted once or several times by --O--.
Claim 10
Dependent Claim
99 words
A coating composition according to claim 8, in which T is alkyl having 1 to 4 carbon atoms, T 1 is hydrogen or chlorine and T 2 is one of the radicals of the formula --OT 3 or --O--T 9 --O-- in which T 3 is hydrogen, alkyl having 1 to 12 carbon atoms or a radical of the formula --C 2 H 4 --(OC 2 H 4 ) 3-7 --H and T 9 is alkylene having 2 to 8 carbon atoms or a radical of the formula --C 2 H 4 --(OC 2 H 4 ) 3-7 --O--.
Claim 11
Dependent Claim
47 words
A coating composition according to claim 9, in which T 2 is a radical of the formula --OT 3 and T 3 is alkyl having 1 to 12 carbon atoms or a radical of the formula --C 2 H 4 --(OC 2 H 4 ) 3-7 --H.
Claim 12
Dependent Claim
139 words
A coating composition according to claim 1, in which, in the compounds of the formula (2), the substituents Y 1 are hydrogen, alkyl having 1 to 12 carbon atoms or halogen, when u is 1, Y 2 is alkyl having 1 to 18 carbon atoms, alkyl which has 1 to 12 carbon atoms and is substituted by, --COOY 8 , --CONY 9 Y 10 and/or --OCOY 11 , glycidyl or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or when u is 2, Y 2 is alkylene having 2 to 16 carbon atoms, alkenylene having 4 to 12 carbon atoms, xylene or alkylene which has 3 to 20 carbon atoms, is interrupted by one or more --O-- atoms and/or is substituted by hydroxyl, the substituents Y 8 to Y 11 being as defined in claim 1.
Claim 13
Dependent Claim
173 words
A coating composition according to claim 11, in which the substituents Y 1 are hydrogen, alkyl having 1 to 4 carbon atoms or chlorine, when u is 1, Y 2 is alkyl which has 1 to 4 carbon atoms and is unsubstituted or substituted by, --COOY 8 , --CONY 9 Y 10 and/or --OCOY 11 , glycidyl or benzyl, or when u is 2, Y 2 is alkylene having 6 to 12 carbon atoms, butenylene, xylylene or alkylene which has 3 to 20 carbon atoms, is interrupted by one or more --O-- atoms and/or is substituted by hydroxyl, Y 8 being alkyl having 4 to 12 carbon atoms, alkenylene having 12 to 18 carbon atoms or alkyl which has 6 to 20 carbon atoms, is interrupted by one or more --O-- atoms and/or is substituted by hydroxyl, Y 9 and Y 10 independently of one another being alkyl having 4 to 8 carbon atoms and Y 11 being alkyl having 1 to 8 carbon atoms or alkenyl having 2 or 3 carbon atoms.
Claim 14
Dependent Claim
106 words
A coating composition according to claim 11, in which u is 1 and r is 2, Y 1 is alkyl having 1 to 4 carbon atoms and Y 2 is alkyl having 1 to 18 carbon atoms or alkyl which has 1 to 12 carbon atoms and is substituted by, --COOY 8 and/or --OCOY 11 , Y 8 being alkyl having 1 to 18 carbon atoms, alkenyl having 3 to 18 carbon atoms or alkyl which has 3 to 20 carbon atoms, is interrupted by one or more oxygen atoms and/or is substituted by hydroxyl, and Y 11 being alkenyl having 2 to 18 carbon atoms.
Claim 15
Dependent Claim
86 words
A coating composition according to claim 13, in which Y 2 is alkyl having 1 to 8 carbon atoms or alkyl which has 1 to 4 carbon atoms and is substituted by, --COOY 8 and/or --OCOY 11 , Y 8 being alkyl having 8 to 12 carbon atoms, alkenyl having 12 to 18 carbon atoms or alkyl which has 5 to 10 carbon atoms, is interrupted by an oxygen atom and is substituted by hydroxyl, and Y 11 being alkenyl having 2 to 8 carbon atoms.
Claim 16
Dependent Claim
70 words
A coating composition according to claim 11, in which Y 1 is methyl and Y 2 is an octyl radical or alkyl which has 1 to 3 carbon atoms and is substituted by, --COOY 8 and/or --OCOY 11 , Y 8 being a decyl or octadecenyl radical or alkyl which has 7 carbon atoms and is substituted by hydroxyl and interrupted by an oxygen atom, and Y 11 being propenyl.
Claim 17
Dependent Claim
39 words
A coating composition according to claim 1, which additionally contains at least one sterically hindered amine, in particular an amine of this type containing at least one radical of the formula ##STR40## in which R is hydrogen or methyl.
Claim 18
Dependent Claim
25 words
A paint film obtainable by applying a coating composition according to claim 1 to a surface and curing the coating composition which has been applied.
References Cited (Backward Citations)
US3268474A
Cited
US4485034A
Cited
US4853471A
Cited
US4973702A
Cited
US4412024A
Cited
US4775707A
Cited
US4619956A
Cited
EP0200190A2
Cited
US4920169A
Cited
US4891396A
Cited
US4996326A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1995-04-21 | 1995-10-21 | 1996-04-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-04-21 | 1999-10-21 | 2000-04-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-04-21 | 2003-10-21 | 2004-04-21 | $7700.00 | Window Closed / Lapsed |