US4289686A
Expired / Lapsed
US
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Tetra-alkyl piperidine derivatives as light stabilizers
Assignee: BASF Corp
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Filing: 1979-09-17
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Granted: 1981-09-15
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Expires: 1999-09-17
Abstract
Abstract Compounds which contain, in their molecule, at least one 2-(2'-hydroxyphenyl)-benztriazole group or one 2-hydroxybenzophenone group and at least one polyalkylpiperidine group are effective light stabilizers for organic materials, in particular for polymers. The use of the compounds as light stabilizers for lacquers is of particular importance.
Inventors
- 👤 Jean Rody
- 👤 Mario Slongo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 10:30
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C09; C09D; C09D7/00; C09D7/40; C09D7/48
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
535 words
A compound of the formula A-B-A, B-A-B, A-Z-B-Z-A or B-Z-A-Z-B wherein A is ##STR13## for compounds of the formulae A-B-A and A-Z-B-Z-A, B is ##STR14## for formula (B XII) wherein R 12 is a free valency; while for compounds of the formulae B-A-B and B-Z-A-Z-B, B is ##STR15## Z is a divalent linking member selected from the group consisting of --(CH 2 ) m --CO--O--, --(CH 2 ) m --CO--O--R 14 --, --O--(CH 2 ) n --CO--O--R 14 --, --CH 2 --CH(OH)--CH 2 --O--CO--(CH 2 ) m , --O--CH 2 --CH(OH)--CH 2 --O--CO--(CH 2 ) m --, --CH 2 --CH(OH)--CH 2 --, --CH 2 --CH(OH)--CH 2 --O--, --CH 2 --CH(OH)--CH 2 --N(R 15 )--(CH 2 ) m --, --O--CH 2 --CH(OH)--CH 2 --N(R 15 )--(CH 2 ) m --, --N(R 15 )--CH 2 --CH(OH)--CH 2 --N(R 16 )--(CH 2 ) m , --CH 2 --CH(R 13 )--O--CH 2 --CH(OH)CH 2 --N(R 15 )--(CH 2 ) m --, --CH 2 --CH(R 13 )--O--CH 2 --CH(OH)--CH 2 --O--CO--(CH 2 ) m --, -- (CH 2 ) m --N(R 15 )--CO--, --(CH 2 ) m --N(R 15 )--CO--(CH 2 ) n --, --O--(CH 2 ) 3 --N(R 15 )--CO--(CH 2 ) m --, --CH 2 --NH--CO--CH 2 --O--, --CH 2 --NH--CO--CH 2 --O--CH(R 13 )--CH 2 --, --CH 2 --NH--CO--CH 2 --N(R 15 )--(CH 2 ) m --, --CH 2 --NH--CO--CH 2 CH 2 --N(R 15 )--(CH 2 ) m -- and ##STR16## one R being hydrogen and one R being a free valency for compounds of the formulae A-B-A and A-Z-B-Z-A, and both R groups being free valency for compounds of the formulae B-A-B and B-Z-A-Z-B; R 1 is hydrogen, chlorine, C 1 -C 4 alkyl, OH or C 1 -C 4 alkoxy; R 2 and R 3 independently of one another are H, Cl, C 1 -C 12 alkyl, C 5 -C 8 cycloalkyl, phenyl, C 7 -C 9 phenylalkyl, OH or C 1 -C 12 alkoxy; R 4 and R 5 independently of one another are H, Cl, OH, C 1 -C 12 alkoxy or C 1 -C 12 alkyl; R 6 is H or CH 3 , R 7 is H, O, C 1 -C 12 alkyl, C 3 -C 8 alkenyl, benzyl, acetyl or a group --CH 2 --CH(OH)--R 13 ; R 8 is C 1 -C 12 alkyl, C 3 -C 8 alkenyl or C 7 -C 9 phenylalkyl; R 9 is a --CH 2 CH═CHCH 2 --; ##STR17## R 10 and R 11 are hydrogen, C 1 -C 12 alkyl, phenyl or benzyl, or R 10 and R 11 are together C 4 -C 19 alkylene; R 12 is H or a free valency; R 13 is H, CH 3 , C 2 H 5 or phenyl; X is a ##STR18## Y is a C 2 -C 8 alkylene group; R 14 is --CH 2 -- or --CH(R 13 )--CH 2 --; R 15 and R 16 are H, C 1 -C 12 -alkyl, cyclohexyl or benzyl; R 17 is --O-- or --NR 15 --; R 18 is C 1 -C 12 -alkoxy, phenoxy or an amino group ##STR19## m is 0, 1 or 2; and n is 1 or 2.
Claim 2
Dependent Claim
535 words
A compound of the formula A-B-A, B-A-B, A-Z-B-Z-A or B-Z-A-Z-B wherein A is ##STR13## for compounds of the formulae A-B-A and A-Z-B-Z-A, B is ##STR14## for formula (B XII) wherein R 12 is a free valency; while for compounds of the formulae B-A-B and B-Z-A-Z-B, B is ##STR15## Z is a divalent linking member selected from the group consisting of --(CH 2 ) m --CO--O--, --(CH 2 ) m --CO--O--R 14 --, --O--(CH 2 ) n --CO--O--R 14 --, --CH 2 --CH(OH)--CH 2 --O--CO--(CH 2 ) m , --O--CH 2 --CH(OH)--CH 2 --O--CO--(CH 2 ) m --, --CH 2 --CH(OH)--CH 2 --, --CH 2 --CH(OH)--CH 2 --O--, --CH 2 --CH(OH)--CH 2 --N(R 15 )--(CH 2 ) m --, --O--CH 2 --CH(OH)--CH 2 --N(R 15 )--(CH 2 ) m --, --N(R 15 )--CH 2 --CH(OH)--CH 2 --N(R 16 )--(CH 2 ) m , --CH 2 --CH(R 13 )--O--CH 2 --CH(OH)CH 2 --N(R 15 )--(CH 2 ) m --, --CH 2 --CH(R 13 )--O--CH 2 --CH(OH)--CH 2 --O--CO--(CH 2 ) m --, -- (CH 2 ) m --N(R 15 )--CO--, --(CH 2 ) m --N(R 15 )--CO--(CH 2 ) n --, --O--(CH 2 ) 3 --N(R 15 )--CO--(CH 2 ) m --, --CH 2 --NH--CO--CH 2 --O--, --CH 2 --NH--CO--CH 2 --O--CH(R 13 )--CH 2 --, --CH 2 --NH--CO--CH 2 --N(R 15 )--(CH 2 ) m --, --CH 2 --NH--CO--CH 2 CH 2 --N(R 15 )--(CH 2 ) m -- and ##STR16## one R being hydrogen and one R being a free valency for compounds of the formulae A-B-A and A-Z-B-Z-A, and both R groups being free valency for compounds of the formulae B-A-B and B-Z-A-Z-B; R 1 is hydrogen, chlorine, C 1 -C 4 alkyl, OH or C 1 -C 4 alkoxy; R 2 and R 3 independently of one another are H, Cl, C 1 -C 12 alkyl, C 5 -C 8 cycloalkyl, phenyl, C 7 -C 9 phenylalkyl, OH or C 1 -C 12 alkoxy; R 4 and R 5 independently of one another are H, Cl, OH, C 1 -C 12 alkoxy or C 1 -C 12 alkyl; R 6 is H or CH 3 , R 7 is H, O, C 1 -C 12 alkyl, C 3 -C 8 alkenyl, benzyl, acetyl or a group --CH 2 --CH(OH)--R 13 ; R 8 is C 1 -C 12 alkyl, C 3 -C 8 alkenyl or C 7 -C 9 phenylalkyl; R 9 is a --CH 2 CH═CHCH 2 --; ##STR17## R 10 and R 11 are hydrogen, C 1 -C 12 alkyl, phenyl or benzyl, or R 10 and R 11 are together C 4 -C 19 alkylene; R 12 is H or a free valency; R 13 is H, CH 3 , C 2 H 5 or phenyl; X is a ##STR18## Y is a C 2 -C 8 alkylene group; R 14 is --CH 2 -- or --CH(R 13 )--CH 2 --; R 15 and R 16 are H, C 1 -C 12 -alkyl, cyclohexyl or benzyl; R 17 is --O-- or --NR 15 --; R 18 is C 1 -C 12 -alkoxy, phenoxy or an amino group ##STR19## m is 0, 1 or 2; and n is 1 or 2.
Claim 3
Dependent Claim
23 words
A compound according to claim 1, which contains a group of the formula (A I), in which R 1 is hydrogen or chlorine.
Claim 4
Dependent Claim
76 words
A compound according to claim 1, in which the groups A are linked to the groups B by one of the groups --(CH 2 ) m --CO--O--, --(CH 2 ) m --CO--O--R 14 --, --O--(CH 2 ) n --CO--O--R 14 --, --(CH 2 ) m --N(R 15 )--CO--, --(CH 2 ) m --N(R 15 )--CO--(CH 2 ) n --, --CH 2 --NH--CO--CH 2 --O-- or --CH 2 --NH--CO--CH 2 --N(R 15 )--(CH 2 ) m --.
Claim 5
Dependent Claim
42 words
A compound according to claim 1, in which the groups A are linked to the groups B by a radical ##STR20## in which R 17 is a group --NR 15 and R 15 and R 18 are as defined in claim 16.
Claim 6
Dependent Claim
24 words
A compound according to claim 1, in which R 6 is hydrogen when B is one or two of the groups BI to BVI.
Claim 7
Dependent Claim
36 words
A compound according to claim 5, in which R 7 is hydrogen, C 1 -C 8 alkyl, allyl or benzyl and R 8 is C 1 -C 12 alkyl, C 3 -C 5 alkenyl or benzyl.
Claim 8
Dependent Claim
10 words
The compound according to claim 1, of the formula ##STR21##
Claim 9
Dependent Claim
30 words
A composition of matter stabilized against light induced deterioration comprising a polymer normally subject to deterioration by light and 0.05 to 5%, by weight, of a compound of claim 1.
Claim 10
Dependent Claim
13 words
The composition of claim 8, wherein said polymer is a binder for lacquers.
Claim 11
Dependent Claim
32 words
A method of stabilizing a polymer normally subject to deterioration by light against said deterioration which comprises incorporating into said polymer an effective stabilizing amount of a compound according to claim 1.
Claim 12
Dependent Claim
13 words
The method of claim 10, wherein said polymer is a binder for lacquers.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-09-14 | 1985-03-16 | 1985-09-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-14 | 1989-03-16 | 1989-09-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-14 | 1993-03-16 | 1993-09-15 | $7700.00 | Window Closed / Lapsed |