← Back to Patent Explorer
US5039722A Expired / Lapsed US ⏱️ 0.0 years remaining

Piperidine-triazine compounds for use as stabilizers for organic materials

Assignee: BASF Corp
•
Filing: 1989-12-21
•
Granted: 1991-08-13
•
Expires: 2009-12-21
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract The new compounds of formula (I) ##STR1## in which R 1 is e.g. hydrogen or methyl, R 2 is e.g. a group --OR 5 or ##STR2## in which R 5 is e.g. 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, R 6 and R 7 which are identical or different are e.g. C 1 -C 8 alkyl, tetrahydrofurfuryl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, or R 6 is also hydrogen, or the group ##STR3## is e.g. 4-morpholinyl, R 3 and R 4 which are identical or different are e.g. hydrogen, methyl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, m and n are e.g. 3, and X is e.g. --O-- or ##STR4## where R 9 is C 1 -C 8 alkyl, tetrahydrofurfuryl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, are effective as light stabilizer, heat stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers.

Inventors

  • 👤 Giuseppe Cantatore
  • 👤 Valerio Borzatta

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 14:08
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/14; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3467; C08K5/3477; C08K5/3492; C08K5/34926

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 478 words
A compound of formula (I) ##STR37## in which R 1 is hydrogen, C 1 -C 8 alkyl, O, OH, NO, CH 2 CN, C 1 -C 18 alkoxy, C 5 -C 12 cycloalkoxy, C 3 -C 5 alkenyl, C 7 -C 9 phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl by C 1 -C 4 alkyl, C 1 -C 8 acyl or C 2 -C 4 alkyl substituted by OH in the 2-, 3- or 4-position, R 2 is a group --OR 5 , --SR 5 or ##STR38## in which R 5 is C 1 -C 18 alkyl, C 3 -C 18 alkyl interrupted by 1, 2 or 3 oxygen atoms, C 2 -C 4 alkyl substituted in the 2-, 3- or 4-position by di-(C 1 -C 4 alkyl)-amino, C 5 -C 12 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, C 3 -C 18 alkenyl, phenyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, C 7 -C 9 phenylalkyl which is uunsubstituted or mono-, di- or tri-substituted on the phenyl by C 1 -C 4 alkyl or a group of the formula (II) ##STR39## where R 8 has any of the definitions of R 1 , R 6 and R 7 which are identical or different are hydrogen, C 1 -C 18 alkyl, C 5 -C 12 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, C 7 -C 9 phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl by C 1 -C 4 alkyl, C 2 -C 4 alkyl which is substituted in the 2-, 3- or 4-position by OH, by C 1 -C 8 alkoxy or by di-(C 1 -C 4 alkyl)-amino, C 3 -C 18 alkenyl, tetrahydrofurfuryl or a group of the formula (II), or the group ##STR40## is a 5- to 7-membered heterocyclic group which is 1-pyrrolidyl, 1-piperidyl, 4-morpholinyl, 4-methyl-1-piperazinyl, 1-hexahydroazepinyl, 5,5,7-trimethyl-1-homopiperazinyl or 4,5,5,7-tetramethyl-1-homopiperazinyl, R 3 and R 4 which are identical or different are hydrogen, C 1 -C 18 alkyl, C 5 -C 12 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, C 7 -C 9 phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl or C 1 -C 4 alkyl or a group of the formula (II), m and n which are identical or different are integers from 2 to 6 and X is --O--or ##STR41## where R 9 is hydrogen, C 1 -C 18 alkyl, C 5 -C 12 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, C 7 -C 9 phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl by C 1 -C 4 alkyl, tetrahydrofurfuryl or a group of the formula (II).
Claim 2
Dependent Claim 478 words
A compound of formula (I) ##STR37## in which R 1 is hydrogen, C 1 -C 8 alkyl, O, OH, NO, CH 2 CN, C 1 -C 18 alkoxy, C 5 -C 12 cycloalkoxy, C 3 -C 5 alkenyl, C 7 -C 9 phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl by C 1 -C 4 alkyl, C 1 -C 8 acyl or C 2 -C 4 alkyl substituted by OH in the 2-, 3- or 4-position, R 2 is a group --OR 5 , --SR 5 or ##STR38## in which R 5 is C 1 -C 18 alkyl, C 3 -C 18 alkyl interrupted by 1, 2 or 3 oxygen atoms, C 2 -C 4 alkyl substituted in the 2-, 3- or 4-position by di-(C 1 -C 4 alkyl)-amino, C 5 -C 12 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, C 3 -C 18 alkenyl, phenyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, C 7 -C 9 phenylalkyl which is uunsubstituted or mono-, di- or tri-substituted on the phenyl by C 1 -C 4 alkyl or a group of the formula (II) ##STR39## where R 8 has any of the definitions of R 1 , R 6 and R 7 which are identical or different are hydrogen, C 1 -C 18 alkyl, C 5 -C 12 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, C 7 -C 9 phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl by C 1 -C 4 alkyl, C 2 -C 4 alkyl which is substituted in the 2-, 3- or 4-position by OH, by C 1 -C 8 alkoxy or by di-(C 1 -C 4 alkyl)-amino, C 3 -C 18 alkenyl, tetrahydrofurfuryl or a group of the formula (II), or the group ##STR40## is a 5- to 7-membered heterocyclic group which is 1-pyrrolidyl, 1-piperidyl, 4-morpholinyl, 4-methyl-1-piperazinyl, 1-hexahydroazepinyl, 5,5,7-trimethyl-1-homopiperazinyl or 4,5,5,7-tetramethyl-1-homopiperazinyl, R 3 and R 4 which are identical or different are hydrogen, C 1 -C 18 alkyl, C 5 -C 12 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, C 7 -C 9 phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl or C 1 -C 4 alkyl or a group of the formula (II), m and n which are identical or different are integers from 2 to 6 and X is --O--or ##STR41## where R 9 is hydrogen, C 1 -C 18 alkyl, C 5 -C 12 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, C 7 -C 9 phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl by C 1 -C 4 alkyl, tetrahydrofurfuryl or a group of the formula (II).
Claim 3
Dependent Claim 37 words
A compound of the formula (I) according to claim 1, in which R 1 is hydrogen, C 1 -C 4 alkyl, OH, C 5 -C 12 alkoxy, C 5 -C 8 cycloalkoxy, allyl, benzyl, acetyl or 2-hydroxyethyl.
Claim 4
Dependent Claim 281 words
A compound of the formula (I) according to claim 1, in which R 2 is a group --OR 5 , --SR 5 or ##STR42## in which R 5 is C 1 -C 12 alkyl, C 3 -C 10 alkyl interrupted by 1, 2 or 3 oxygen atoms, C 2 -C 3 alkyl substituted in the 2- or 3-position by di-(C 1 -C 4 alkyl)-amino, C 5 -C 8 cycloalkyl which is unsubstitued or mono-, di- or tri-substituted by C 1 -C 4 alkyl, C 3 -C 12 alkenyl, phenyl, benzyl or a group of the formula (II), R 6 and R 7 which are identical or different are hydrogen, C 1 -C 12 alkyl, C 5 -C 8 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 , benzyl, C 2 -C 3 alkyl substituted in the 2- or 3-position by OH, by C 1 -C 4 alkoxy or by di-(C 1 -C 4 alkyl)-amino, allyl, oleyl, tetrahydrofurfuryl or a group of the formula (II), or the group ##STR43## is 1-pyrrolidyl, 1-piperidyl, 4-morpholinyl, 4-methyl-1-piperazinyl or 1-hexahydroazepinyl, R 3 and R 4 which are identical or different are hydrogen, C 1 -C 12 alkyl, C 5 -C 8 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, benzyl or a group of the formula (II), m and n which are identical or different are 2 or 3, and X is --O-- or ##STR44## where R 9 is hydrogen, C 1 -C 12 alkyl, C 5 -C 8 cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, benzyl, tetrahydrofurfuryl or a group of the formula (II).
Claim 5
Dependent Claim 248 words
A compound of the formula (I) according to claim 1, in which R 2 is a group --OR 5 or ##STR45## in which R 5 is C 1 -C 8 alkyl, C 4 -C 10 alkyl interrupted by 1 or 2 oxygen atoms, C 2 -C 3 alkyl substituted in the 2- or 3-position by dimethylamino or diethylamino, cyclohexyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, allyl, undecenyl, phenyl, benzyl, or a group of the formula (II), R 6 and R 7 which are identical or different are hydrogen, C 1 -C 12 alkyl, cyclohexyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, benzyl, C 2 -C 3 alkyl substituted in the 2- or 3-position by OH, by methoxy, by ethoxy, by dimethylamino or by diethylamino, allyl, tetrahydrofurfuryl or a group of the formula (II) or the group ##STR46## is 4-morpholinyl or 4-methyl-1-piperazinyl, R 3 and R 4 which are identical or different are hydrogen, C 1 -C 8 alkyl, cyclohexyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, benzyl or a group of the formula (II), m and n which are identical or different are 2 or 3, and X is --O-- or ##STR47## where R 9 is hydrogen, C 1 -C 12 alkyl, cyclohexyl which is unsubstituted or mono-, di- or tri-substituted by C 1 -C 4 alkyl, benzyl, tetrahydrofurfuryl or a group of the formula (II).
Claim 6
Dependent Claim 136 words
A compound of the formula (I) according to claim 1, in which R 2 is a group --OR 5 or ##STR48## in which R 5 is C 1 -C 4 alkyl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, R 6 and R 7 which are identical or different are C 1 -C 8 alkyl, cyclohexyl, benzyl, C 2 -C 3 alkyl substituted in the 2- or 3-position by methoxy, by ethoxy, by dimethylamino or by diethylamino, allyl, tetrahydrofurfuryl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, or R 6 is also hydrogen or the group ##STR49## is 4-morpholinyl, R 3 and R 4 which are identical or different are hydrogen, C 1 -C 4 alkyl, cyclohexyl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, m and n are 3, and X is --O-- or ##STR50## where R 9 is C 1 -C 8 alkyl, cyclohexyl, benzyl, tetrahydrofurfuryl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl.
Claim 7
Dependent Claim 107 words
A compound of the formula (I) according to claim 1, in which R 1 is hydrogen or methyl, R 2 is a group --OR 5 or ##STR51## in which R 5 is 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, R 6 and R 7 which are identical or different are C 1 -C 8 alkyl, tetrahydrofurfuryl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, or R 6 is also hydrogen, or the group ##STR52## is 4-morpholinyl, R 3 and R 4 which are identical or different are hydrogen, methyl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, m and n are 3, and X is --O-- or ##STR53## where R 9 is C 1 -C 8 alkyl, tetrahydrofurfuryl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl.
Claim 8
Dependent Claim 23 words
The compound of the formula ##STR54## in which the radicals R 1 are equal and are hydrogen or methyl, according to claim 1.
Claim 9
Dependent Claim 35 words
A composition containing an a polymer, oil, fat or wax susceptible to degradation induced by light, heat or oxidation and an effective stabilizing amount of a compound of the formula (I) according to claim 1.
Claim 10
Dependent Claim 13 words
A composition according to claim 8, wherein the polymer is a synthetic polymer.
Claim 11
Dependent Claim 24 words
A composition according to claim 9 which, in addition to the compound of the formula (I), also contains other conventional additives for synthetic polymers.
Claim 12
Dependent Claim 12 words
A composition according to claim 8, wherein the polymer is a polyolefin.
Claim 13
Dependent Claim 13 words
A composition according to claim 8, wherein the polymer is polyethylene or polypropylene.
Claim 14
Dependent Claim 41 words
A method for stabilizing an a polymer, oil, fat or wax against degradation induced by light, heat or oxidation, which comprises incorporating into said organic material an effective stabilizing amount of a compound of the formula (I) according to claim 1.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-08-12 1995-02-11 1995-08-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-08-12 1999-02-11 1999-08-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-08-12 2003-02-11 2003-08-13 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag