US5026749A
Expired / Lapsed
US
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Piperidine compounds for use as light stabilizers, heat stabilizers and oxidation stabilizers for organic material
Assignee: BASF Corp
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Filing: 1990-05-14
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Granted: 1991-06-25
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Expires: 2010-05-14
Abstract
Abstract The novel compounds of the formula (I) ##STR1## in which n is 1 or 2, R 1 is hydrogen, O·, OH, NO, CH 2 CN, C 1 -C 8 -alkyl, allyl, benzyl, hydroxyalkyl, alkoxy, cycloalkoxy or acyl, R 2 is alkyl, cycloalkyl, phenylalkyl, alkoxyalkyl, tetrahydrofurfuryl or a group of the formula (II) and A is a monovalent or divalent moiety, in which R 1 is as defined above, and, if n=1, A is a group of the formula (III) in which each R 9 independently is hydrogen or methyl, r is zero or 1 and are useful as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials.
Inventors
- 👤 Giuseppe Cantatore
- 👤 Valerio Borzatta
- 👤 Franca Masina
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 17:24
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/58; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
283 words
A compound of the formula (I) ##STR56## in which n is 1 or 2, R 1 is hydrogen, O.sup.., OH, NO, CH 2 CN, C 1 -C 8 -alkyl, allyl, benzyl, OH-monosubstituted C 2 -C 4 -alkyl, C 1 -C 18 -alkyloxy, C 5 -C 12 -cycloalkyloxy or C 1 -C 8 -acyl, R 2 is C 1 -C 18 -alkyl, C 5 -C 12 -cycloalkyl, C 7 -C 12 -phenylalkyl, C 1 -C 12 -alkoxy-monosubstituted C 2 -C 4 -alkyl, tetrahydrofurfuryl or a group of the formula (II) ##STR57## in which R 1 is as defined above, and, when n=1, A is a group of the formula (III) ##STR58## in which R 1 is as defined above, R 3 is as defined for R 2 and p is an integer from 1 to 5, or, when n=2, A is a group of the formula (IV), (V), (VI) or (VII) ##STR59## in which p is as defined above, R 4 is as defined above for R 2 , R 5 is C 2 -C 12 -alkylene, C 6 -C 15 -cycloalkylene or xylylene, Z is a group of the formula (VIII) ##STR60## in which R 1 , R 2 and p are as defined above, R 6 and R 8 which are identical or different are C 1 -C 8 -alkyl, cyclohexyl, benzyl or a group of the formula (II) and R 7 is C 2 -C 12 -alkylene, C 6 -C 15 -cycloalkylene or xylylene, or the group ##STR61## is a heterocyclic radical of the formula (IX) or (X) ##STR62## in which each R 9 independently is hydrogen or methyl, r is zero or 1 and R 2 is as defined above.
Claim 2
Dependent Claim
283 words
A compound of the formula (I) ##STR56## in which n is 1 or 2, R 1 is hydrogen, O.sup.., OH, NO, CH 2 CN, C 1 -C 8 -alkyl, allyl, benzyl, OH-monosubstituted C 2 -C 4 -alkyl, C 1 -C 18 -alkyloxy, C 5 -C 12 -cycloalkyloxy or C 1 -C 8 -acyl, R 2 is C 1 -C 18 -alkyl, C 5 -C 12 -cycloalkyl, C 7 -C 12 -phenylalkyl, C 1 -C 12 -alkoxy-monosubstituted C 2 -C 4 -alkyl, tetrahydrofurfuryl or a group of the formula (II) ##STR57## in which R 1 is as defined above, and, when n=1, A is a group of the formula (III) ##STR58## in which R 1 is as defined above, R 3 is as defined for R 2 and p is an integer from 1 to 5, or, when n=2, A is a group of the formula (IV), (V), (VI) or (VII) ##STR59## in which p is as defined above, R 4 is as defined above for R 2 , R 5 is C 2 -C 12 -alkylene, C 6 -C 15 -cycloalkylene or xylylene, Z is a group of the formula (VIII) ##STR60## in which R 1 , R 2 and p are as defined above, R 6 and R 8 which are identical or different are C 1 -C 8 -alkyl, cyclohexyl, benzyl or a group of the formula (II) and R 7 is C 2 -C 12 -alkylene, C 6 -C 15 -cycloalkylene or xylylene, or the group ##STR61## is a heterocyclic radical of the formula (IX) or (X) ##STR62## in which each R 9 independently is hydrogen or methyl, r is zero or 1 and R 2 is as defined above.
Claim 3
Dependent Claim
210 words
A compound of the formula (I) according to claim 1, in which n is 1 or 2, R 1 is hydrogen, CH 2 CN, C 1 -C 4 -alkyl, allyl, benzyl, OH-monosubstituted C 2 -C 3 -alkyl or acetyl, R 2 is C 1 -C 12 -alkyl, C 5 -C 9 -cycloalkyl, benzyl, C 1 -C 8 -alkoxy-monosubstituted C 2 -C 3 -alkyl, tetrahydrofurfuryl or a group of the formula (II) and, when n=1, A is a group of the formula (III) in which R 1 is as defined above, R 3 is as defined for R 2 and p is an integer from 1 to 3, or, when n=2, A is one of the groups of the formulae (IV), (V), (VI) or (VII) in which p is as defined above, R 4 is as defined above for R 2 , R 5 is C 2 -C 6 -alkylene or C 6 -C 13 -cycloalkylene, Z is a group of the formula (VIII) with R 1 , R 2 and p being as defined above, R 6 and R 8 are a group of the formula (II) and R 7 is C 2 -C 6 -alkylene or C 6 -C 13 -cycloalkylene, or the group ##STR63## is 1,4-piperazinediyl or 5,5,7-trimethyl-1,4-homopiperazinediyl.
Claim 4
Dependent Claim
178 words
A compound of the formula (I) according to claim 1, in which n is 1 or 2, R 2 is C 1 -C 12 -alkyl, cyclohexyl, benzyl, C 1 -C 4 -alkoxy-monosubstituted C 2 -C 3 -alkyl or a group of the formula (II) and, when n=1, A is a group of the formula (III) with R 1 being as defined in claim 1, R 3 being as defined for R 2 and p being 1 or 2, or, when n=2, A is a group of the formula (IV), (V), (VI) or (VII) in which p is 1 or 2, R 4 is as defined above for R 2 , R 5 is C 2 -C 6 -alkylene and Z is a group of the formula (VIII) with R 1 being as defined in claim 1, R 2 and p being as defined above, R 6 and R 8 are a group of the formula (II) and R 7 is C 2 -C 6 -alkylene, or the group ##STR64## is a group of the formula (X) or 1,4-piperazinediyl.
Claim 5
Dependent Claim
18 words
A compound of the formula (I) according to claim 1, in which R 1 is hydrogen or methyl.
Claim 6
Dependent Claim
175 words
A compound of the formula (I) according to claim 1, in which n is 1 or 2, R 1 is hydrogen or methyl, R 2 is C 1 -C 12 -alkyl, cyclohexyl, benzyl, C 1 -C 4 -alkoxy-monosubstituted C 2 -C 3 -alkyl or a group of the formula (II) with R 1 being hydrogen or methyl and, when n=1, A is a group of the formula (III) with R 1 being hydrogen or methyl, R 3 being as defined above for R 2 and p being 1 or 2, or, when n=2, A is a group of the formula (IV), (V), (VI) or (VII) in which p is 1 or 2, R 4 is as defined above for R 2 , R 5 is C 2 -C 6 -alkylene and Z is a group of the formula (VIII) with R 1 , R 2 and p being as defined above, R 6 and R 8 are 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl and R 7 is C 2 -C 6 -alkylene, or the group ##STR65## is 1,4-piperazinediyl.
Claim 7
Dependent Claim
154 words
A compound of the formula (I) according to claim 1, in which n is 1 or 2, R 1 is hydrogen or methyl, R 2 is C 1 -C 12 -alkyl and, when n=1, A is a group of the formula (III) in which R 1 is hydrogen or methyl, R 3 is C 1 -C 12 -alkyl and p is 1, or, when n=2, A is a group of the formula (IV), (V) or (VII) in which p is 1, R 4 is C 1 -C 12 -alkyl, cyclohexyl, benzyl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, R 5 is C 2 -C 6 -alkylene, Z is a group of the formula (VIII) in which R 1 is hydrogen or methyl, R 2 is C 1 -C 12 -alkyl and p is 1, R 6 and R 8 are 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl and R 7 is C 2 -C 6 -alkylene, or the group ##STR66## is 1,4-piperazinediyl.
Claim 8
Dependent Claim
15 words
A compound of the formula (I) according to claim 1, in which n is 2.
Claim 9
Dependent Claim
81 words
A compound of the formula (I) according to claim 1, in which n is 2, R 1 is hydrogen or methyl, R 2 is C 1 -C 8 -alkyl, A is a group of the formula (IV) or (VII) in which p is 1, R 4 is C 4 -C 12 -alkyl, cyclohexyl, benzyl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, R 6 and R 8 are 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl and R 7 is C 2 -C 6 -alkylene or the group ##STR67## is 1,4-piperazinediyl.
Claim 10
Dependent Claim
10 words
A compound of the formula ##STR68## according to claim 1.
Claim 11
Dependent Claim
29 words
A composition comprising an organic material subject to thermal, oxidative or light-induced degradation and an effective stabilizing amount of a compound of the formula (I) according to claim 1.
Claim 12
Dependent Claim
14 words
A composition according to claim 10, wherein the organic material is a synthetic polymer.
Claim 13
Dependent Claim
24 words
A composition according to claim 11, which, in addition to the compound of the formula (I), also comprises other conventional additives for synthetic polymers.
Claim 14
Dependent Claim
13 words
A composition according to claim 10, wherein the organic material is a polyolefine.
Claim 15
Dependent Claim
14 words
A composition according to claim 10, wherein the organic material is polyethylene or polypropylene.
Claim 16
Dependent Claim
35 words
A method for stabilizing an organic material against thermal, oxidative or light-induced degradation, which comprises incorporating into the organic material an effective stabilizing amount of a compound of the formula (I) according to claim 1.
References Cited (Backward Citations)
GB1318559A
Cited
GB1401924A
Cited
US4500662A
Cited
US4618634A
Cited
US4578454A
Cited
EP0172413A2
Cited
JPS6263570A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-06-24 | 1994-12-24 | 1995-06-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-06-24 | 1998-12-24 | 1999-06-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-06-24 | 2002-12-24 | 2003-06-25 | $7700.00 | Window Closed / Lapsed |