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US4185007A Expired / Lapsed US ⏱️ 0.0 years remaining

Barbituric acid derivatives containing a phenolic moiety and/or a hindered amine moiety

Assignee: BASF Corp
•
Filing: 1977-06-24
•
Granted: 1980-01-22
•
Expires: 1997-06-24
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Abstract

Abstract New barbituric acid derivatives containing at least one phenolic moiety and at least one hindered amine moiety are effective lightstabilizers and antioxidants.

Inventors

  • 👤 Michael Rasberger
  • 👤 Friedrich Karrer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 19:32
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/60; C07D239/62; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442; C08K5/3462

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 549 words
A compound of the formula I ##STR18## in which R is hydrogen or one of the groups ##STR19## or an addition salt of formula III, wherein one of R 3 and R 5 is --OH and the other is hydrogen, R 4 denotes C 1 -C 12 alkyl, C 5 -C 7 cycloalkyl, phenyl, α-naphthyl, β-naphthyl or C 7 -C 9 aralkyl, R 6 and R 7 are hydrogen, C 1 -C 12 alkyl, C 5 -C 7 cycloalkyl, phenyl, α-naphthyl, β-naphthyl or C 7 -C 9 aralkyl, R 8 is hydrogen or C 1 -C 8 alkyl and R 9 is hydrogen, oxyl, C 1 -C 12 alkyl, C 3 -C 6 alkenyl, C 3 -C 4 alkinyl, C 2 -C 21 alkoxyalkyl, C 7 -C 8 aralkyl, 2,3-epoxypropyl, an aliphatic acyl group of a carboxylic acid with 1-4 C atoms, or one of the groups --CH 2 COOR 10 , --CH 2 --CH(R 11 )--OR 12 , --COOR 13 or --CONHR 13 , wherein R 10 is C 1 -C 14 alkyl, C 3 -C 6 alkenyl, phenyl, C 7 -C 8 aralkyl or cyclohexyl, R 11 is hydrogen, methyl or phenyl, R 12 denotes hydrogen, benzoyl, an aliphatic, phenylaliphatic or alicyclic acyl group of a carboxylic acid with 1-18 C atoms, wherein the phenyl moiety of the benzoyl and phenylaliphatic acyl groups can optionally be substituted by one or two chlorine atoms, one or two C 1 -C 4 alkyl groups or one C 1 -C 8 alkoxy group, and/or substituted by one hydroxyl group, and R 13 denotes C 1 -C 12 alkyl, cyclohexyl, phenyl or benzyl, X is --O--or --NR 14 -- wherein R 14 denotes hydrogen or C 1 -C 12 alkyl, and n denotes 1 to 5, and, if R is hydrogen or a group of formula II, R 1 denotes hydrogen, C 1 -C 18 alkyl, C 5 -C 7 cycloalkyl, a group of the formula II or a group of the formula R 15 --CO--(C n H 2n )-- (IV) wherein n has the meaning defined above and R 15 denotes C 1 -C 18 alkyl, C 5 -C 7 cycloalkyl, C 1 -C 18 alkoxy, C 5 -C 7 cycloalkoxy, C 7 -C 9 aralkyl or a group of the formula ##STR20## or an addition salt of formula V, wherein X, R 8 and R 9 have the meaning defined above, and, if R is a group of the formula III, R 1 denotes hydrogen or a group of the formula II, and, if R is hydrogen or a group of the formula II, R 2 denotes a group of the formula III or VI ##STR21## wherein R 8 and R 9 have the meaning defined above, and, if R is a group of the formula III, R 2 denotes hydrogen, C 1 -C 18 alkyl, C 5 -C 7 cycloalkyl, phenyl, α-naphthyl, β-naphthyl, C 7 -C 9 aralkyl or one of the groups II, III or V, with the proviso that said compound of formula I contains at least one phenolic moiety of the formula II and at least one hindered amine moiety selected from the group consisting of formula III, and addition salt of formula III, formula V, an addition salt of formula V, and formula VI.
Claim 2
Dependent Claim 549 words
A compound of the formula I ##STR18## in which R is hydrogen or one of the groups ##STR19## or an addition salt of formula III, wherein one of R 3 and R 5 is --OH and the other is hydrogen, R 4 denotes C 1 -C 12 alkyl, C 5 -C 7 cycloalkyl, phenyl, α-naphthyl, β-naphthyl or C 7 -C 9 aralkyl, R 6 and R 7 are hydrogen, C 1 -C 12 alkyl, C 5 -C 7 cycloalkyl, phenyl, α-naphthyl, β-naphthyl or C 7 -C 9 aralkyl, R 8 is hydrogen or C 1 -C 8 alkyl and R 9 is hydrogen, oxyl, C 1 -C 12 alkyl, C 3 -C 6 alkenyl, C 3 -C 4 alkinyl, C 2 -C 21 alkoxyalkyl, C 7 -C 8 aralkyl, 2,3-epoxypropyl, an aliphatic acyl group of a carboxylic acid with 1-4 C atoms, or one of the groups --CH 2 COOR 10 , --CH 2 --CH(R 11 )--OR 12 , --COOR 13 or --CONHR 13 , wherein R 10 is C 1 -C 14 alkyl, C 3 -C 6 alkenyl, phenyl, C 7 -C 8 aralkyl or cyclohexyl, R 11 is hydrogen, methyl or phenyl, R 12 denotes hydrogen, benzoyl, an aliphatic, phenylaliphatic or alicyclic acyl group of a carboxylic acid with 1-18 C atoms, wherein the phenyl moiety of the benzoyl and phenylaliphatic acyl groups can optionally be substituted by one or two chlorine atoms, one or two C 1 -C 4 alkyl groups or one C 1 -C 8 alkoxy group, and/or substituted by one hydroxyl group, and R 13 denotes C 1 -C 12 alkyl, cyclohexyl, phenyl or benzyl, X is --O--or --NR 14 -- wherein R 14 denotes hydrogen or C 1 -C 12 alkyl, and n denotes 1 to 5, and, if R is hydrogen or a group of formula II, R 1 denotes hydrogen, C 1 -C 18 alkyl, C 5 -C 7 cycloalkyl, a group of the formula II or a group of the formula R 15 --CO--(C n H 2n )-- (IV) wherein n has the meaning defined above and R 15 denotes C 1 -C 18 alkyl, C 5 -C 7 cycloalkyl, C 1 -C 18 alkoxy, C 5 -C 7 cycloalkoxy, C 7 -C 9 aralkyl or a group of the formula ##STR20## or an addition salt of formula V, wherein X, R 8 and R 9 have the meaning defined above, and, if R is a group of the formula III, R 1 denotes hydrogen or a group of the formula II, and, if R is hydrogen or a group of the formula II, R 2 denotes a group of the formula III or VI ##STR21## wherein R 8 and R 9 have the meaning defined above, and, if R is a group of the formula III, R 2 denotes hydrogen, C 1 -C 18 alkyl, C 5 -C 7 cycloalkyl, phenyl, α-naphthyl, β-naphthyl, C 7 -C 9 aralkyl or one of the groups II, III or V, with the proviso that said compound of formula I contains at least one phenolic moiety of the formula II and at least one hindered amine moiety selected from the group consisting of formula III, and addition salt of formula III, formula V, an addition salt of formula V, and formula VI.
Claim 3
Dependent Claim 374 words
A compound, according to claim 1, of the formula I in which R denotes hydrogen or one of the groups of the formula II or III, wherein R 3 is hydrogen, R 4 denotes C 1 -C 12 alkyl, R 5 is --OH, R 6 is hydrogen or C 1 -C 12 alkyl, R 7 denotes hydrogen or C 1 -C 6 alkyl, R 8 is hydrogen or C 1 -C 4 alkyl and R 9 is hydrogen, oxyl, C 1 -C 8 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkinyl, C 2 -C 6 alkoxyalkyl, C 7 -C 8 aralkyl, acetyl, acryloyl, crotonoyl or one of the groups --CH 2 --COOR 10 , --CH 2 --CH(R 11 )--OR 12 , --COOR 13 or --CONHR 13 , wherein R 10 is C 1-C 4 alkyl, C 3 -C 4 alkenyl, phenyl, C 7 -C 8 aralkyl or cyclohexyl, R 11 is hydrogen, methyl or phenyl, R 12 denotes hydrogen, benzoyl, an aliphatic, phenylaliphatic or alicyclic acyl group of a carboxylic acid with 1-18 C atoms, wherein the phenyl moiety of the benzoyl and phenylaliphatic acyl groups can optionally be substituted by one or two chlorine atoms, one or two C 1 -C 4 alkyl groups or one C 1 -C 8 alkoxy group, and/or substituted by one hydroxyl group, and R 13 is C 1 -C 12 alkyl, X is --O-- or --NR 14 -- wherein R 14 denotes hydrogen or C 1 -C 12 alkyl, n denotes 1 to 5 and, if R is hydrogen or a group of the formula II, R 1 denotes C 1 -C 18 alkyl, cyclohexyl, a group of the formula II or a group of the formula IV, wherein R 15 is C 1 -C 18 alkyl, or is a group of the formula V and, if R is a group of the formula III, R 1 denotes a group of the formula II and, if R is hydrogen or a group of the formula II, R 2 denotes a group of the formula III or VI and, if R is a group of the formula III, R 2 denotes C 1 -C 18 alkyl or one of the groups II, III or V.
Claim 4
Dependent Claim 233 words
A compound, according to claim 1, of the formula I in which R denotes hydrogen or a group of the formula II wherein R 3 denotes hydrogen, R 4 denotes C 1 -C 6 alkyl, R 5 is --OH, R 6 denotes hydrogen or C 1 -C 6 alkyl, R 7 denotes hydrogen or C 1 -C 4 alkyl, R 1 denotes C 1 -C 18 alkyl, a group of the formula II or a group of the formula IV, wherein R 15 is C 1 -C 18 alkyl or a group of the formula V wherein R 8 denotes hydrogen, methyl or ethyl and R 9 is hydrogen, C 1 -C 4 alkyl, allyl, propargyl, C 2 -C 6 alkoxyalkyl, acetyl, acryloyl, crotonyl or one of the groups --CH 2 --COOR 10 , --CH 2 --CH(R 11 )--OR 12 , --COOR 13 or --CONHR 13 , wherein R 10 is C 1 -C 4 alkyl, R 11 denotes hydrogen or methyl, R 12 denotes hydrogen and R 13 is C 1 -C 4 alkyl, X is --O-- or --NR 14 -- wherein R 14 is hydrogen or methyl, n denotes 1 to 3 and R 2 denotes one of the groups III or VI, wherein the radicals R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the meaning defined above.
Claim 5
Dependent Claim 117 words
A compound, according to claim 1, of the formula I in which R denotes hydrogen or a group of the formula II wherein R 3 and R 6 are hydrogen, R 4 denotes C 1 -C 4 alkyl, R 5 denotes --OH, R 7 denotes hydrogen or methyl, R 1 denotes a group of the formula II or IV, wherein R 15 is a group of the formula V wherein R 8 is hydrogen and R 9 is hydrogen, methyl or acetyl, and X denotes --O-- or --NH--, n is 1 to 3 and R 2 denotes one of the groups III or VI, wherein the radicals R 8 and R 9 have the meaning defined above.
Claim 6
Dependent Claim 14 words
A compound, according to claim 1, of the formula I wherein n denotes 1.
Claim 7
Dependent Claim 33 words
A composition comprising a plastic and a compound of the formula I according to claim 1, in an amount which is effective to stabilize said plastic against degradation by oxygen, heat or light.
Claim 8
Dependent Claim 46 words
A method of stabilizing a plastic against degradation by oxygen, heat or light, which comprises incorporating in said plastic a compound of the formula I according to claim 1, in an amount which is effective to stabilize said plastic against degradation by oxygen, heat or light.
Claim 9
Dependent Claim 29 words
A compound according to claim 1, which is selected from the group consisting of 1,3-di-[3,5-di-t.butyl-4-hydroxy-benzyl]-5,5-di-[2-(1,2,2,6,6-pentamethyl-piperidin-4-yl-oxy)-carbonyl-n-propyl]-barbituric acid, 1,3-di-[3-methyl-5-t.butyl-4-hydroxybenzyl]-5-[(2,2,6,6-tetramethyl-piperidin-4-yl-imino)-carbonylethyl]-barbituric acid, 1,3-di-[3,5-di-t.butyl-4-hydroxybenzyl]-5,5-di-[(2,2,6,6-tetramethyl-piperidin-4-yl-oxy)-carbonyolmethyl]-barbituric acid, 1,3,5-tris-[3,5-di-t.butyl-4-hydroxybenzyl]-5-[2-(2,2,6,6-tetramethyl-piperidin-4-yl-oxy)-carbonylpropyl]-barbituric acid, 1,3,5-tris-[2,6-dimethyl-4-t.butyl-3-hydroxybenzyl]-5-[(2,2,6,6-tetramethylpiperidin-4-yl]-barbituric acid, 1,3,5-tris-[2-(2,2,6,6-tetramethylpiperidin-4-yl-oxy)-carbonylethyl]-5-[3,5-di-t.butyl-4-hydroxybenzyl]-barbituric acid, and 1,3-di-[2,3,6-trimethyl-2,6-diethylpiperidin-4-yl-imino)-carbonylmethyl]-5-octyl-5-(3,5-di-t.butyl-4-hydroxybenzyl)-barbituric acid.
Claim 10
Dependent Claim 25 words
A composition according to claim 6, containing 0.01 to 5% by weight of the compound of formula I, based on the weight of the plastic.
Claim 11
Dependent Claim 18 words
A composition according to claim 6, wherein the plastic is a polyolefine, a styrene polymer or a polyurethane.

References Cited (Backward Citations)

US3930006A Cited
US3636080A Cited
US4028334A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-01-21 1983-07-23 1984-01-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-01-21 1987-07-23 1988-01-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-01-21 1991-07-23 1992-01-22 $7700.00 Window Closed / Lapsed

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