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US4234728A
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Polyalkylpiperidine derivatives of s-triazine
Assignee: BASF Corp
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Filing: 1978-12-21
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Granted: 1980-11-18
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Expires: 1998-12-21
Abstract
Abstract s-Triazine derivatives which contain, as substituents in the 2-, 4- and 6-position, at least one polyalkylpiperidine radical and at least one N-methylolamino group or an ether thereof, are effective stabilisers for plastics, in particular against light degradation. By virtue of their N-methylol group, they are able to enter into a chemical bond with many plastics and this renders them stable to migration and elution.
Inventors
- 👤 Jean Rody
- 👤 Godwin Berner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 20:44
CPC Classifications
C; C09; C09D; C09D167/00; C09D167/08; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3477; C08K5/3492; C08K5/34926; C09D5/00; C09D5/38; C09D7/00; C09D7/40; C09D7/48
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
505 words
A compound of the formula I or II ##STR29## in which m is an integer from 1 to 4 and n is a value from 2 to 50, X and X' are --O--, --S-- or --NR 6 --, in which R 6 is hydrogen, C 1 -C 18 alkyl, C 3 -C 8 alkenyl, C 1 -C 4 hydroxyalkyl, C 2 -C 13 alkoxyalkyl, C 5 -C 12 cycloalkyl, C 6 -C 10 aryl, C 7 -C 9 phenylalkyl, or a polyalkylpiperidine group of the formula III ##STR30## in which R is hydrogen or methyl, p is 0 or 1, A is C 1 -C 4 -alkylene, --NR 6 --C 2 -C 12 -alkylene- or --OCH 2 CH 2 CH 2 -- and R 7 is H, O, C 1 -C 12 -alkyl, allyl, benzyl or a --CH 2 --CH(R 8 )--OH group, in which R 8 is H, CH 3 , C 2 H 5 or phenyl, and R 1 and R 3 are hydrogen, C 1 -C 18 alkyl, C 3 -C 8 alkenyl, C 1 -C 4 hydroxyalkyl, C 2 -C 13 alkoxyalkyl, C 5 -C 12 cycloalkyl, C 6 -C 10 aryl, C 7 -C 9 phenylalkyl, phenyl or phenylalkyl which is substituted by one or more substituents from the group consisting of C 1 -C 8 alkyl, OH, C 1 -C 4 alkoxy, and a polyalkylpiperidine group of the formula III, R 2 is hydrogen, C 1 -C 18 alkyl, C 3 -C 8 alkenyl, C 2 -C 6 hydroxyalkyl or C 3 -C 6 alkoxyalkyl, R 4 , if m is 1, is hydrogen, C 1 -C 18 alkyl, C 3 -C 8 alkenyl, C 2 -C 4 hydroxyalkyl, C 3 -C 6 alkoxyalkyl, C 6 -C 10 aryl, C 7 -C 9 phenylalkyl, phenyl or phenylalkyl which is substituted by one or more substituents from the group consisting of C 1 -C 8 alkyl, OH, C 1 -C 4 alkoxy, and a polyalkylpiperidine group of the formula III, and, if m is 2, C 2 -C 12 alkylene or oxaalkylene, C 4 -C 12 alkenylene, C 6 -C 10 arylene, a -phenylene-Z-phenylene- radical, in which Z is --O--, --S--, --SO 2 --, --CH 2 -- or --C(CH 3 ) 2 --, or a radical of the formula --(CH 2 ) r --N(Y)--(CH 2 ) r --N(Y)] q (CH 2 ) r --, wherein r is 2 or 3 and q is 0 or 1 and Y is a triazinyl group of the formula IV, ##STR31## and, if m is 3, is a R 8 --C(CH 2 --) 3 radical, in which R 8 is C 1 -C 4 alkyl, and, if m is 4, is a C(CH 2 --) 4 radical, R 5 is C 2 -C 12 alkylene and E is hydrogen, alkyl or HX--R 5 -- and E' is XH and at least one of the radicals R 1 , R 3 , R 4 , or R 6 is a polyalkylpiperidine of the formula III.
Claim 2
Dependent Claim
505 words
A compound of the formula I or II ##STR29## in which m is an integer from 1 to 4 and n is a value from 2 to 50, X and X' are --O--, --S-- or --NR 6 --, in which R 6 is hydrogen, C 1 -C 18 alkyl, C 3 -C 8 alkenyl, C 1 -C 4 hydroxyalkyl, C 2 -C 13 alkoxyalkyl, C 5 -C 12 cycloalkyl, C 6 -C 10 aryl, C 7 -C 9 phenylalkyl, or a polyalkylpiperidine group of the formula III ##STR30## in which R is hydrogen or methyl, p is 0 or 1, A is C 1 -C 4 -alkylene, --NR 6 --C 2 -C 12 -alkylene- or --OCH 2 CH 2 CH 2 -- and R 7 is H, O, C 1 -C 12 -alkyl, allyl, benzyl or a --CH 2 --CH(R 8 )--OH group, in which R 8 is H, CH 3 , C 2 H 5 or phenyl, and R 1 and R 3 are hydrogen, C 1 -C 18 alkyl, C 3 -C 8 alkenyl, C 1 -C 4 hydroxyalkyl, C 2 -C 13 alkoxyalkyl, C 5 -C 12 cycloalkyl, C 6 -C 10 aryl, C 7 -C 9 phenylalkyl, phenyl or phenylalkyl which is substituted by one or more substituents from the group consisting of C 1 -C 8 alkyl, OH, C 1 -C 4 alkoxy, and a polyalkylpiperidine group of the formula III, R 2 is hydrogen, C 1 -C 18 alkyl, C 3 -C 8 alkenyl, C 2 -C 6 hydroxyalkyl or C 3 -C 6 alkoxyalkyl, R 4 , if m is 1, is hydrogen, C 1 -C 18 alkyl, C 3 -C 8 alkenyl, C 2 -C 4 hydroxyalkyl, C 3 -C 6 alkoxyalkyl, C 6 -C 10 aryl, C 7 -C 9 phenylalkyl, phenyl or phenylalkyl which is substituted by one or more substituents from the group consisting of C 1 -C 8 alkyl, OH, C 1 -C 4 alkoxy, and a polyalkylpiperidine group of the formula III, and, if m is 2, C 2 -C 12 alkylene or oxaalkylene, C 4 -C 12 alkenylene, C 6 -C 10 arylene, a -phenylene-Z-phenylene- radical, in which Z is --O--, --S--, --SO 2 --, --CH 2 -- or --C(CH 3 ) 2 --, or a radical of the formula --(CH 2 ) r --N(Y)--(CH 2 ) r --N(Y)] q (CH 2 ) r --, wherein r is 2 or 3 and q is 0 or 1 and Y is a triazinyl group of the formula IV, ##STR31## and, if m is 3, is a R 8 --C(CH 2 --) 3 radical, in which R 8 is C 1 -C 4 alkyl, and, if m is 4, is a C(CH 2 --) 4 radical, R 5 is C 2 -C 12 alkylene and E is hydrogen, alkyl or HX--R 5 -- and E' is XH and at least one of the radicals R 1 , R 3 , R 4 , or R 6 is a polyalkylpiperidine of the formula III.
Claim 3
Dependent Claim
11 words
A compound according to claim 1, in which R is hydrogen.
Claim 4
Dependent Claim
17 words
A compound according to claim 1, in which X and X' are a --NR 6 -- group.
Claim 5
Dependent Claim
192 words
A compound according to claim 1 of the formula I, in which m is 1 or 2, X and X' are a --NR 6 -- group, in which R 6 is hydrogen, C 3 -C 8 alkyl, C 1 -C 2 hydroxyalkyl, C 2 -C 4 alkoxyalkyl, cyclohexyl, benzyl or a polyalkyl-piperidine group of the formula III, R 1 and R 3 are hydrogen, C 1 -C 4 alkyl, C 1 -C 2 hydroxyalkyl, C 2 -C 3 alkoxyalkyl or a piperidine radical of the formula III, in which p is nought, R is hydrogen and R 7 is hydrogen, C 1 -C 4 alkyl or hydroxyethyl, R 2 is hydrogen, C 1 -C 4 alkyl or allyl and R 4 , if m is 1, is hydrogen, C 1 -C 4 alkyl, hydroxyethyl, benzyl or a polyalkylpiperidine radical of the formula III, and if m is 2 is C 2 -C 6 alkylene, -phenylene-CH 2 -phenylene or a radical --CH.sub. 2 CH 2 --N(Y)--CH 2 CH 2 --N(Y)] q CH 2 CH 2 --, in which q is nought or 1 and Y is a triazinyl group of the formula IV.
Claim 6
Dependent Claim
122 words
A compound according to claim 1, of the formula II, in which n is 2 to 10, X is a --NR 6 -- group, in which R 6 is hydrogen, C 3 -C 8 alkyl, C 1 -C 2 hydroxyalkyl, C 2 -C 4 alkoxyalkyl, cyclohexyl, benzyl or a polyalkylpiperidine group of the formula III, R 1 is hydrogen, C 1 -C 4 alkyl, C 1 -C 2 hydroxyalkyl, C 2 -C 3 alkoxyalkyl or a polyalkylpiperidine radical of the formula III, in which p is nought, R is hydrogen and R 7 is hydrogen, C 1 -C 4 alkyl or hydroxyethyl, R 2 is hydrogen, C 1 -C 4 alkyl or allyl and R 5 is C 2 -C 8 alkylene.
Claim 7
Dependent Claim
5 words
2,4-Bis-[N-(2,2,6,6-tetramethyl-4-piperidyl)butylamino]-6-dimethylolamino-1,3,5-triazine according to claim 1.
Claim 8
Dependent Claim
5 words
2,4-Bis-(N-methylol-ethylamino)-6-[N-(2,2,6,6-tetramethyl-4-piperidyl)-butylamino]-1,3,5-triazine according to claim 1.
Claim 9
Dependent Claim
5 words
2,4-Bis-[N(2,2,6,6-tetramethyl-4-piperidyl)-β-hydroxy-ethylamino]-6-N-methoxymethyl-tert-octylamino-1,3,5-triazine according to claim 1.
Claim 10
Dependent Claim
5 words
N,N'-Bis-(2,2,6,6-tetramethyl-4-piperidyl)-N,N'-bis[2-di(methoxymethylamino-4-N-(2,2,6,6-tetramethyl-4-piperidyl)-butylamino-1,3,5-triazin-6-yl]-hexamethylenediamine according to claim 1.
References Cited (Backward Citations)
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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) | 1983-11-18 | 1984-05-19 | 1984-11-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-18 | 1988-05-19 | 1988-11-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-18 | 1992-05-19 | 1992-11-18 | $7700.00 | Window Closed / Lapsed |