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US4609698A Expired / Lapsed US ⏱️ 0.0 years remaining

Oligoesters containing polyalkylpiperidine groups

Assignee: BASF Corp
•
Filing: 1985-04-26
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Granted: 1986-09-02
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Expires: 2005-04-26
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Abstract

Abstract Oligomeric esters of the formula I or II ##STR1## in which n has a value from 1 to 3, R 1 and R 2 are divalent organic radicals, at least one of which contains a polyalkylpiperidine radical of the formula III ##STR2## in which R is hydrogen or C 1 -C 4 -alkyl and E and E' are end groups, are prepared by polycondensing a dicarboxylic acid ester with a diol, one of the two components being used in a molar excess of 33 to 100%. The end groups of these oligoesters can be modified by reaction with a monofunctional component. If two different dicarboxylic acid esters or diols are used, the corresponding co-oligoesters are obtained. All these oligoesters are valuable light stabilisers for light-sensitive organic material, especially for polymer.

Inventors

  • 👤 Friedrich Karrer
  • 👤 Jean Rody

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 21:26
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; C07D211/56; C07D211/58

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 587 words
An oligomeric ester of the formula I or II ##STR23## in which n has a value from 1 to 3, R 1 and R 2 are divalent organic radicals at least one of which contains a polyalkylpiperidine radical, R 1 is C 2 -C 18 -alkylene, C 4 -C 8 -alkenylene, C 4 -C 20 -monooxaalkylene, C 4 -C 20 -polyoxaalkylene, C 5 -C 8 -cycloalkylene, C 7 -C 10 -cycloalkane-dialkylene, C 8 -C 20 -arene-dialkylene or a divalent radical of the formulae ##STR24## in which m is 2 to 10, X is a group --O-- or --NR 5 --, Y is C 2 -C 12 -alkylene, C 4 -C 12 -alkylene which is interrupted by one or two --O-- or --NH-- groups, cyclohexylene, cyclohexane dimethylene, C 6 -C 12 -arylene or -phenylene-Z-phenylene- in which Z is --O--, --CH 2 --, or --SO 2 --, R 2 is a direct bond, C 1 -C 18 -alkylene, C 2 -C 6 -alkenylene, C 5 -C 8 -cycloalkylene, C 5 -C 8 -cycloalkenylene, C 6 -C 12 -arylene, C 7 -C 12 -aralkylene or a divalent radical of the formulae ##STR25## in which p is 1 or 2, E is hydrogen, C 1 -C 8 -alkyl, cyclohexyl, benzyl or an acyl group of the formula R 7 --CO--, R 8 --O--CO-- or (R 9 )(R 10 )N--CO-- and E' is a group R 11 O-- or (R 12 )(R 13 )N-- and wherein R 3 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 7 -alkoxymethyl, phenoxymethyl or tolyloxymethyl, R 4 is hydrogen, C 1 -C 8 -alkyl, C 2 -C 8 -alkanoyl, C 3 -C 6 -alkenoyl, C 7 -C 12 -phenylalkyl or C 3 -C 5 -alkenylmethyl, R 5 is hydrogen, C 1 -C 12 -alkyl, cyclohexyl, phenyl, benzyl, phenylethyl, C 2 -C 8 -alkanoyl, C 3 -C 6 -alkenoyl or benzoyl, R 6 is C 2 -C 12 -alkylene, C 4 -C 8 -alkenylene or xylylene, R 7 is C 1 -C 12 -alkyl, C 2 -C 5 -alkenyl, C 5 -C 8 -cycloalkyl, C 6 -C 10 -aryl, C.sub. 7 -C 12 -phenylalkyl or a group of the formula ##STR26## R 8 is C 1 -C 12 -alkyl, allyl, cyclohexyl or phenyl, R 9 is hydrogen, C 1 -C 8 -alkyl, allyl, cyclohexyl, phenyl or C 7 -C 10 -alkylphenyl and R 10 is C 1 -C 8 -alkyl, allyl, cyclohexyl, phenyl or C 7 -C 10 -alkylphenyl, or R 9 and R 10 , together with the N atom to which they are attached, form a pyrrolidine, piperidine, morpholine, 4-methylpiperazine or 4-(2-cyanoethyl)piperazine ring, R 11 is C 1 -C 12 -alkyl, C 3 -C 5 -alkenylmethyl, C 5 -C 8 -cycloalkyl, phenyl, C 7 -C 10 -alkylphenyl, C 7 -C 12 -phenylalkyl, C 3 -C 12 -alkoxyalkyl, a group --(CH 2 CH 2 O) m --CH 3 , a group of the formula IV or a group of the formula V ##STR27## R 12 is C 1 -C 12 -alkyl, allyl, cyclohexyl, phenyl, benzyl, C 3 -C 12 -alkoxyalkyl, C 4 -C 12 -dialkylaminoalkyl, a group of the formula IV or a group of the formula VI ##STR28## and R 13 is hydrogen, C 1 -C 12 -alkyl, allyl, cyclohexyl or a group of the formula IV, and to co-oligomers thereof, said oligomeric ester being formed by the polycondensation of a dicarboxylic acid ester and a diol, one of which components being in a molar excess of 33 to 100% of the other.
Claim 2
Dependent Claim 587 words
An oligomeric ester of the formula I or II ##STR23## in which n has a value from 1 to 3, R 1 and R 2 are divalent organic radicals at least one of which contains a polyalkylpiperidine radical, R 1 is C 2 -C 18 -alkylene, C 4 -C 8 -alkenylene, C 4 -C 20 -monooxaalkylene, C 4 -C 20 -polyoxaalkylene, C 5 -C 8 -cycloalkylene, C 7 -C 10 -cycloalkane-dialkylene, C 8 -C 20 -arene-dialkylene or a divalent radical of the formulae ##STR24## in which m is 2 to 10, X is a group --O-- or --NR 5 --, Y is C 2 -C 12 -alkylene, C 4 -C 12 -alkylene which is interrupted by one or two --O-- or --NH-- groups, cyclohexylene, cyclohexane dimethylene, C 6 -C 12 -arylene or -phenylene-Z-phenylene- in which Z is --O--, --CH 2 --, or --SO 2 --, R 2 is a direct bond, C 1 -C 18 -alkylene, C 2 -C 6 -alkenylene, C 5 -C 8 -cycloalkylene, C 5 -C 8 -cycloalkenylene, C 6 -C 12 -arylene, C 7 -C 12 -aralkylene or a divalent radical of the formulae ##STR25## in which p is 1 or 2, E is hydrogen, C 1 -C 8 -alkyl, cyclohexyl, benzyl or an acyl group of the formula R 7 --CO--, R 8 --O--CO-- or (R 9 )(R 10 )N--CO-- and E' is a group R 11 O-- or (R 12 )(R 13 )N-- and wherein R 3 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 7 -alkoxymethyl, phenoxymethyl or tolyloxymethyl, R 4 is hydrogen, C 1 -C 8 -alkyl, C 2 -C 8 -alkanoyl, C 3 -C 6 -alkenoyl, C 7 -C 12 -phenylalkyl or C 3 -C 5 -alkenylmethyl, R 5 is hydrogen, C 1 -C 12 -alkyl, cyclohexyl, phenyl, benzyl, phenylethyl, C 2 -C 8 -alkanoyl, C 3 -C 6 -alkenoyl or benzoyl, R 6 is C 2 -C 12 -alkylene, C 4 -C 8 -alkenylene or xylylene, R 7 is C 1 -C 12 -alkyl, C 2 -C 5 -alkenyl, C 5 -C 8 -cycloalkyl, C 6 -C 10 -aryl, C.sub. 7 -C 12 -phenylalkyl or a group of the formula ##STR26## R 8 is C 1 -C 12 -alkyl, allyl, cyclohexyl or phenyl, R 9 is hydrogen, C 1 -C 8 -alkyl, allyl, cyclohexyl, phenyl or C 7 -C 10 -alkylphenyl and R 10 is C 1 -C 8 -alkyl, allyl, cyclohexyl, phenyl or C 7 -C 10 -alkylphenyl, or R 9 and R 10 , together with the N atom to which they are attached, form a pyrrolidine, piperidine, morpholine, 4-methylpiperazine or 4-(2-cyanoethyl)piperazine ring, R 11 is C 1 -C 12 -alkyl, C 3 -C 5 -alkenylmethyl, C 5 -C 8 -cycloalkyl, phenyl, C 7 -C 10 -alkylphenyl, C 7 -C 12 -phenylalkyl, C 3 -C 12 -alkoxyalkyl, a group --(CH 2 CH 2 O) m --CH 3 , a group of the formula IV or a group of the formula V ##STR27## R 12 is C 1 -C 12 -alkyl, allyl, cyclohexyl, phenyl, benzyl, C 3 -C 12 -alkoxyalkyl, C 4 -C 12 -dialkylaminoalkyl, a group of the formula IV or a group of the formula VI ##STR28## and R 13 is hydrogen, C 1 -C 12 -alkyl, allyl, cyclohexyl or a group of the formula IV, and to co-oligomers thereof, said oligomeric ester being formed by the polycondensation of a dicarboxylic acid ester and a diol, one of which components being in a molar excess of 33 to 100% of the other.
Claim 3
Dependent Claim 122 words
An oligomer as claimed in claim 1 of the formula I or II in which n has a value from 1 to 3, R 1 is a group of the formula ##STR29## R 2 is C 1 -C 12 -alkylene, C 2 -C 12 -alkenylene or phenylene, E is hydrogen or a group R 7 --CO-- and E' is a group R 11 --O--, R 3 is hydrogen, C 1 -C 4 -alkyl, C 2 -C 6 -alkoxymethyl, phenoxymethyl or tolyloxymethyl, R 4 is hydrogen, C 1 -C 4 -alkyl, acetyl, allyl or benzyl, R 7 is C 1 -C 6 -alkyl or phenyl and R 11 is C 1 -C 12 -alkyl or a group of the formula IV or V.
Claim 4
Dependent Claim 25 words
An oligoester as claimed in claim 1, which is obtained by reacting dimethyl sebacate with 1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine or with 1-(2-hydroxypropyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine in a molar ratio of 3:2.
Claim 5
Dependent Claim 22 words
An oligoester as claimed in claim 1, which is obtained by reacting diethyl adipate with 1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine in a molar ratio of 3:2.
Claim 6
Dependent Claim 22 words
An oligoester as claimed in claim 1, which is obtained by reacting dimethyl isophthalate with 1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine in a molar ratio of 3:2.
Claim 7
Dependent Claim 22 words
An oligoester as claimed in claim 1, which is obtained by reacting dimethyl 2,2,4-trimethylglutarate with 1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine in a molar ratio of 3:2.
Claim 8
Dependent Claim 33 words
A method of stabilizing organic material against damage caused by light and UV radiation, by adding an effective amount of at least one compound of the formula I or II of claim 10.
Claim 9
Dependent Claim 11 words
A method as claimed in claim 7 of stabilizing organic polymers.

References Cited (Backward Citations)

US4233412A Cited
US4234707A Cited
US4210576A Cited
US4237297A Cited
US4314933A Cited
US4348524A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-09-01 1990-03-03 1990-09-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-09-01 1994-03-03 1994-09-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-09-01 1998-03-03 1998-09-02 $7700.00 Window Closed / Lapsed

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