US4198334A
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Substituted malonic acid derivatives and their use as stabilizers
Assignee: BASF Corp
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Filing: 1977-12-15
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Granted: 1980-04-15
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Expires: 1997-12-15
Abstract
Abstract Esters and amides from 4-hydroxy-and 4-amino-polyalkylpiperidines and hydroxybenzylmalonic acids substituted at the central carbon atom with an organic residue, preferably alkyl-, esteralkyl- or phosphonoalkyl-groups, are excellent stabilizers for organic polymers, especially for polyolefins. They protect the polymers as well against light degradation as against thermo-oxidative degradation. The compounds can be prepared by hydroxybenzylation of the corresponding derivatives of substituted malonic acids. Bis-malonic acid derivatives may be obtained from the monomalonics by reaction with formaldehyde.
Inventors
- 👤 Michael Rasberger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 13:11
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; C07D211/92; C07D211/94; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/40; C07F9/4003; C07F9/4006; C07F9/547; C07F9/553; C07F9/576; C07F9/58; C07F9/59; C08K5/0008; C08K5/005
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
803 words
A member selected from the group consisting of a compound of the formula (I) ##STR60## and an acid addition salt thereof, wherein n is 1 or 2, R a represents alkyl having 1-6 carbon atoms, R b represents alkyl having 1-6 carbon atoms, R c represents alkyl having 1-9 carbon atoms, phenyl, benzyl or phenylethyl, R d represents alkyl having 1-6 carbon atoms, or R c and R d together represent tetra- or pentamethylene, R e represents hydrogen, alkyl having 1-5 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms or aralkyl having 7-8 carbon atoms, R f represents hydrogen, alkyl having 1-5 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms, or aralkyl having 7-8 carbon atoms, with R e and R f being mutually exchangeable, and X represents oxygen or --NR--, R represents hydrogen, alkyl having 1-18 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms, cycloalkyl having 5-12 carbon atoms, aryl having 6-10 carbon atoms, or aralkyl having 7-9 carbon atoms, R 1 represents hydrogen, --O.sup.., --OH, alkyl having 1-12 carbon atoms, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or a group of the formula --CH 2 --CH(OR 5 )--R 4 wherein R 4 represents hydrogen, methyl or phenyl, and R 5 represents hydrogen or a group A--CO--, or R 1 represents a group A--CO--, and in both cases A represents alkyl having 1-12 carbon atoms, alkenyl having 2 or 3 carbon atoms, cyclohexyl, phenyl, benzyl, a phenyl or phenylethyl group substituted by 2 alkyl groups each having 1-4 carbon atoms and a hydroxyl group, alkylamino having 1-12 carbon atoms, dialkylamino having 2-16 carbon atoms, anilino, alkoxy having 1-12 carbon atoms, benzyloxy or phenoxy, R 2 represents a hydroxybenzyl group of the formula II ##STR61## wherein R 6 and R 7 each independently represent an alkyl group having 1-9 carbon atoms, aralkyl having 7-9 carbon atoms or cycloalkyl having 5-8 carbon atoms, and R 8 represents hydrogen or methyl, and R 3 represents, in the case where n is 1, alkyl having 1-20 carbon atoms, or alkyl having 1-10 carbon atoms, which is substituted by at least one of the groups --OR 9 , --SR 10 , --CO-R 11 , --CN, --C(O)--YR 12 , --O--C(O)R 13 or --P(O)(OR 14 ) 2 , wherein R 9 denotes phenyl or alkylphenyl having 7-10 carbon atoms, benzyl or cyclohexyl, R 10 represents phenyl or alkylphenyl having 7-10 carbon atoms, R 11 denotes alkyl having 1-12 carbon atoms, Y denotes oxygen or --NR--, and R has the above-given meaning, R 12 denotes alkyl having 1-18 carbon atoms, cycloalkyl having 5-12 carbon atoms, or a group of the formula III ##STR62## wherein R 17 has one of the meanings given for R 1 R 13 denotes alkyl having 1-17 carbon atoms, cycloalkyl having 5-12 carbon atoms, or phenyl or phenylalkyl having 7-9 carbon atoms, wherein the phenyl radical is unsubstituted or substituted by at least one of the groups alkyl having 1-4 carbon atoms and hydroxyl, and R 14 denotes alkyl having 1-8 carbon atoms, allyl or phenyl, and X has the above-defined meaning, and R 3 further represents an alkyl group having 2-22 carbon atoms, which is interrupted by --O--, --S--, --SO-- or --SO 2 --, alkenyl having 3-18 carbon atoms, alkynyl having 3-8 carbon atoms, cycloalkyl having 5-12 carbon atoms, alkyl-cycloalkyl having 6-18 carbon atoms, cycloalkyl-alkyl having 6-14 carbon atoms, aralkyl or alkyl-aralkyl having 7-19 carbon atoms, phenyl, or a group --OR 15 , wherein R 15 is alkyl having 1-18 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms, cycloalkyl having 5-12 carbon atoms or aralkyl having 7-9 carbon atoms, or R 3 represents a group --O--C(O)R 16 or --NH--C(O)R 16 , wherein R 16 is alkyl having 1-12 carbon atoms, alkenyl having 2 or 3 carbon atoms, cyclohexyl, phenyl, benzyl, a phenyl or phenylethyl group substituted by 2 alkyl groups each having 1- 4 carbon atoms and a hydroxyl group, or R 3 is a group of the formula III or of the formula IV ##STR63## wherein R 18 represents alkyl having 1-20 carbon atoms, allyl, benzyl, phenyl, cyclohexyl, alkoxyalkyl- having 3-8 carbon atoms, or a group --O--C(O)R 16 or --NH--C(O)R 16 as defined above, or has one of the meanings given for R 2 , and R 19 and R 20 each independently represent alkyl having 1-6 carbon atoms, or a radical of the formula III, and, in addition, R 3 represents, in the case where n is 2, a direct bond, alkylene having 1-20 carbon atoms, alkylene having 2-20 carbon atoms, which is interrupted by one or two of the members --O--, --S--, --SO--, --SO 2 -- or --CO--O--, arylene-bis-alkylene having 8-14 carbon atoms, alkenylene having 4-8 carbon atoms, or alkynylene having 4-8 carbon atoms.
Claim 2
Dependent Claim
803 words
A member selected from the group consisting of a compound of the formula (I) ##STR60## and an acid addition salt thereof, wherein n is 1 or 2, R a represents alkyl having 1-6 carbon atoms, R b represents alkyl having 1-6 carbon atoms, R c represents alkyl having 1-9 carbon atoms, phenyl, benzyl or phenylethyl, R d represents alkyl having 1-6 carbon atoms, or R c and R d together represent tetra- or pentamethylene, R e represents hydrogen, alkyl having 1-5 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms or aralkyl having 7-8 carbon atoms, R f represents hydrogen, alkyl having 1-5 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms, or aralkyl having 7-8 carbon atoms, with R e and R f being mutually exchangeable, and X represents oxygen or --NR--, R represents hydrogen, alkyl having 1-18 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms, cycloalkyl having 5-12 carbon atoms, aryl having 6-10 carbon atoms, or aralkyl having 7-9 carbon atoms, R 1 represents hydrogen, --O.sup.., --OH, alkyl having 1-12 carbon atoms, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or a group of the formula --CH 2 --CH(OR 5 )--R 4 wherein R 4 represents hydrogen, methyl or phenyl, and R 5 represents hydrogen or a group A--CO--, or R 1 represents a group A--CO--, and in both cases A represents alkyl having 1-12 carbon atoms, alkenyl having 2 or 3 carbon atoms, cyclohexyl, phenyl, benzyl, a phenyl or phenylethyl group substituted by 2 alkyl groups each having 1-4 carbon atoms and a hydroxyl group, alkylamino having 1-12 carbon atoms, dialkylamino having 2-16 carbon atoms, anilino, alkoxy having 1-12 carbon atoms, benzyloxy or phenoxy, R 2 represents a hydroxybenzyl group of the formula II ##STR61## wherein R 6 and R 7 each independently represent an alkyl group having 1-9 carbon atoms, aralkyl having 7-9 carbon atoms or cycloalkyl having 5-8 carbon atoms, and R 8 represents hydrogen or methyl, and R 3 represents, in the case where n is 1, alkyl having 1-20 carbon atoms, or alkyl having 1-10 carbon atoms, which is substituted by at least one of the groups --OR 9 , --SR 10 , --CO-R 11 , --CN, --C(O)--YR 12 , --O--C(O)R 13 or --P(O)(OR 14 ) 2 , wherein R 9 denotes phenyl or alkylphenyl having 7-10 carbon atoms, benzyl or cyclohexyl, R 10 represents phenyl or alkylphenyl having 7-10 carbon atoms, R 11 denotes alkyl having 1-12 carbon atoms, Y denotes oxygen or --NR--, and R has the above-given meaning, R 12 denotes alkyl having 1-18 carbon atoms, cycloalkyl having 5-12 carbon atoms, or a group of the formula III ##STR62## wherein R 17 has one of the meanings given for R 1 R 13 denotes alkyl having 1-17 carbon atoms, cycloalkyl having 5-12 carbon atoms, or phenyl or phenylalkyl having 7-9 carbon atoms, wherein the phenyl radical is unsubstituted or substituted by at least one of the groups alkyl having 1-4 carbon atoms and hydroxyl, and R 14 denotes alkyl having 1-8 carbon atoms, allyl or phenyl, and X has the above-defined meaning, and R 3 further represents an alkyl group having 2-22 carbon atoms, which is interrupted by --O--, --S--, --SO-- or --SO 2 --, alkenyl having 3-18 carbon atoms, alkynyl having 3-8 carbon atoms, cycloalkyl having 5-12 carbon atoms, alkyl-cycloalkyl having 6-18 carbon atoms, cycloalkyl-alkyl having 6-14 carbon atoms, aralkyl or alkyl-aralkyl having 7-19 carbon atoms, phenyl, or a group --OR 15 , wherein R 15 is alkyl having 1-18 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms, cycloalkyl having 5-12 carbon atoms or aralkyl having 7-9 carbon atoms, or R 3 represents a group --O--C(O)R 16 or --NH--C(O)R 16 , wherein R 16 is alkyl having 1-12 carbon atoms, alkenyl having 2 or 3 carbon atoms, cyclohexyl, phenyl, benzyl, a phenyl or phenylethyl group substituted by 2 alkyl groups each having 1- 4 carbon atoms and a hydroxyl group, or R 3 is a group of the formula III or of the formula IV ##STR63## wherein R 18 represents alkyl having 1-20 carbon atoms, allyl, benzyl, phenyl, cyclohexyl, alkoxyalkyl- having 3-8 carbon atoms, or a group --O--C(O)R 16 or --NH--C(O)R 16 as defined above, or has one of the meanings given for R 2 , and R 19 and R 20 each independently represent alkyl having 1-6 carbon atoms, or a radical of the formula III, and, in addition, R 3 represents, in the case where n is 2, a direct bond, alkylene having 1-20 carbon atoms, alkylene having 2-20 carbon atoms, which is interrupted by one or two of the members --O--, --S--, --SO--, --SO 2 -- or --CO--O--, arylene-bis-alkylene having 8-14 carbon atoms, alkenylene having 4-8 carbon atoms, or alkynylene having 4-8 carbon atoms.
Claim 3
Dependent Claim
28 words
A compound according to claim 1 wherein R a , R b , R c , R d are methyl, and R e and R f are hydrogen.
Claim 4
Dependent Claim
286 words
A compound according to claim 1 wherein X is --O-- or --NH--, R 1 is hydrogen, --O.sup.., --OH, alkyl having 1-4 carbon atoms, allyl, propargyl, acetyl, acryloyl or crotonyl, R 2 is a hydroxybenzyl group of the formula IIa or IIb ##STR64## R 6 and R 7 each independently represent alkyl having 1-4 carbon atoms, R 8 represents hydrogen or methyl, R 3 represents in the case where n is 1 alkyl having 1-18 carbon atoms, alkyl having 1-4 carbon atoms which is substituted by one or two of the groups --CN, --C(O)--YR 12 , --O--C(O)R 13 or --P(O)(OR 14 ) 2 , wherein Y is --O-- or --NH--, R 12 is alkyl having 1-4 carbon atoms, or a group of the formula IIIb ##STR65## R 13 can be alkyl having 1-17 carbon atoms, cyclohexyl, phenyl or benzyl, and R 14 can be alkyl having 1-4 carbon atoms or allyl, and R 3 further represents alkyl having 2-18 carbon atoms which is interrupted by --O-- or --S--, cycloalkyl having 5-12 carbon atoms, alkylcycloalkyl having 6-18 carbon atoms, alkenyl having 3-6 carbon atoms, alkynyl having 3-6 carbon atoms, phenyl, aralkyl having 7-15 carbon atoms, or a group --OR 15 , wherein R 15 represents alkyl having 1-12 carbon atoms, allyl, propargyl or benzyl, or a group --O--COR 16 or --NH--COR 16 , wherein R 16 represents alkyl having 1-12 carbon atoms, phenyl, 3,5-di-tert.butyl-4-hydroxyphenyl, or 2-(3,5-di-tert.butyl-4-hydroxyphenyl)-ethyl, or a group of the formula IIIb, or in the case where n is 2, R 3 represents a direct bond, alkylene having 1-12 carbon atoms which can be interrupted by one or two of the groups --O--, --S-- or --CO--O--, arylene-bis-alkylene having 8-14 carbon atoms or alkenylene having 4-8 carbon atoms.
Claim 5
Dependent Claim
562 words
A member of the group consisting of a compound of the formula Ia ##STR66## and an acid addition salt thereof, wherein n is 1 or 2, R a represents alkyl having 1-6 carbon atoms, R b represents alkyl having 1-6 carbon atoms, R c represents alkyl having 1-9 carbon atoms, phenyl benzyl or phenylethyl, R d represents alkyl having 1-6 carbon atoms, or R c and R d together represent tetra- or pentamethylene, R e represents hydrogen, alkyl having 1-5 carbon atoms, alkenyl or alkynyl having 3-4 carbon atoms or aralkyl having 7-8 carbon atoms, R f represents hydrogen, alkyl having 1-5 carbon atoms, alkenyl or alkynyl having 3-4 carbon atoms, or aralkyl having 7-8 carbon atoms, with R e and R f being mutually exchangeable, and R 1 represents hydrogen, --O.sup.., --OH, alkyl having 1-12 carbon atoms, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or a group of the formula --CH 2 --CH(OR 5 )--R 4 wherein R 4 represents hydrogen, methyl or phenyl, and R 5 represents hydrogen or a group A--CO--, or R 1 represents a group A--CO--, and in both cases A represents alkyl having 1-12 carbon atoms, alkenyl having 2 or 3 carbon atoms, cyclohexyl, phenyl, benzyl, a phenyl or phenylethyl group substituted by 2 alkyl groups each having 1-4 carbon atoms and a hydroxyl group, alkylamino having 1-12 carbon atoms, dialkylamino having 2-16 carbon atoms, anilino, alkoxy having 1-12 carbon atoms, benzyloxy or phenoxy, R 2 represents a hydroxybenzyl group of the formula II ##STR67## wherein R 6 and R 7 each independently represent an alkyl group having 1-9 carbon atoms, aralkyl having 7-9 carbon atoms or cycloalkyl having 5-8 carbon atoms, and R 8 represents hydrogen or methyl, and R 3 represents, in the case where n is 1, alkyl having 1-20 carbon atoms, or alkyl having 1-10 carbon atoms, which is substituted by one of the groups --OR 9 , --SR 10 , --CO--R 11 , --CN, --CO--OR 12 , --O--C(O)R 13 or --P(O)(OR 14 ) 2 , wherein R 9 denotes phenyl or alkylphenyl having 7-10 carbon atoms, benzyl or cyclohexyl, R 10 represents phenyl or alkylphenyl having 7-10 carbon atoms, R 11 denotes alkyl having 1-12 carbon atoms, R 12 denotes having 1-18 carbon atoms, cycloalkyl having 5-12 carbon atoms, or a group of the formula IIIb ##STR68## R 13 denotes alkyl having 1-17 carbon atoms, cycloalkyl having 5-12 carbon atoms, or phenyl or phenylalkyl having 7-9 carbon atoms, wherein the phenyl radical is unsubstituted or substituted by at least one of the groups alkyl having 1-4 carbon atoms and hydroxyl, and R 14 denotes alkyl having 1-8 carbon atoms, allyl or phenyl, and R 3 further represents an alkyl group having 2-22 carbon atoms, which is interrupted by --O--, --S--, --SO-- or --SO 2 --, alkenyl having 3-18 carbon atoms, alkynyl having 3-8 carbon atoms, cycloalkyl having 5-12 carbon atoms, alkyl-cycloalkyl having 6-18 carbon atoms, cycloalkyl-alkyl having 6-14 carbon atoms, aralkyl or alkyl-aralkyl having 7-19 carbon atoms, or phenyl, and, in addition R 3 represents, in the case where n is 2, a direct bond, alkylene having 1-20 carbon atoms, alkylene having 2-20 carbon atoms, which is interrupted by one or two of the members --O--, --S--, --SO--, --SO 2 -- or --CO--O--, arylene-bis-alkylene having 8-14 carbon atoms, alkenylene having 4-8 carbon atoms, or alkynylene having 4-8 carbon atoms.
Claim 6
Dependent Claim
562 words
A member of the group consisting of a compound of the formula Ia ##STR66## and an acid addition salt thereof, wherein n is 1 or 2, R a represents alkyl having 1-6 carbon atoms, R b represents alkyl having 1-6 carbon atoms, R c represents alkyl having 1-9 carbon atoms, phenyl benzyl or phenylethyl, R d represents alkyl having 1-6 carbon atoms, or R c and R d together represent tetra- or pentamethylene, R e represents hydrogen, alkyl having 1-5 carbon atoms, alkenyl or alkynyl having 3-4 carbon atoms or aralkyl having 7-8 carbon atoms, R f represents hydrogen, alkyl having 1-5 carbon atoms, alkenyl or alkynyl having 3-4 carbon atoms, or aralkyl having 7-8 carbon atoms, with R e and R f being mutually exchangeable, and R 1 represents hydrogen, --O.sup.., --OH, alkyl having 1-12 carbon atoms, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or a group of the formula --CH 2 --CH(OR 5 )--R 4 wherein R 4 represents hydrogen, methyl or phenyl, and R 5 represents hydrogen or a group A--CO--, or R 1 represents a group A--CO--, and in both cases A represents alkyl having 1-12 carbon atoms, alkenyl having 2 or 3 carbon atoms, cyclohexyl, phenyl, benzyl, a phenyl or phenylethyl group substituted by 2 alkyl groups each having 1-4 carbon atoms and a hydroxyl group, alkylamino having 1-12 carbon atoms, dialkylamino having 2-16 carbon atoms, anilino, alkoxy having 1-12 carbon atoms, benzyloxy or phenoxy, R 2 represents a hydroxybenzyl group of the formula II ##STR67## wherein R 6 and R 7 each independently represent an alkyl group having 1-9 carbon atoms, aralkyl having 7-9 carbon atoms or cycloalkyl having 5-8 carbon atoms, and R 8 represents hydrogen or methyl, and R 3 represents, in the case where n is 1, alkyl having 1-20 carbon atoms, or alkyl having 1-10 carbon atoms, which is substituted by one of the groups --OR 9 , --SR 10 , --CO--R 11 , --CN, --CO--OR 12 , --O--C(O)R 13 or --P(O)(OR 14 ) 2 , wherein R 9 denotes phenyl or alkylphenyl having 7-10 carbon atoms, benzyl or cyclohexyl, R 10 represents phenyl or alkylphenyl having 7-10 carbon atoms, R 11 denotes alkyl having 1-12 carbon atoms, R 12 denotes having 1-18 carbon atoms, cycloalkyl having 5-12 carbon atoms, or a group of the formula IIIb ##STR68## R 13 denotes alkyl having 1-17 carbon atoms, cycloalkyl having 5-12 carbon atoms, or phenyl or phenylalkyl having 7-9 carbon atoms, wherein the phenyl radical is unsubstituted or substituted by at least one of the groups alkyl having 1-4 carbon atoms and hydroxyl, and R 14 denotes alkyl having 1-8 carbon atoms, allyl or phenyl, and R 3 further represents an alkyl group having 2-22 carbon atoms, which is interrupted by --O--, --S--, --SO-- or --SO 2 --, alkenyl having 3-18 carbon atoms, alkynyl having 3-8 carbon atoms, cycloalkyl having 5-12 carbon atoms, alkyl-cycloalkyl having 6-18 carbon atoms, cycloalkyl-alkyl having 6-14 carbon atoms, aralkyl or alkyl-aralkyl having 7-19 carbon atoms, or phenyl, and, in addition R 3 represents, in the case where n is 2, a direct bond, alkylene having 1-20 carbon atoms, alkylene having 2-20 carbon atoms, which is interrupted by one or two of the members --O--, --S--, --SO--, --SO 2 -- or --CO--O--, arylene-bis-alkylene having 8-14 carbon atoms, alkenylene having 4-8 carbon atoms, or alkynylene having 4-8 carbon atoms.
Claim 7
Dependent Claim
750 words
A member selected from the group consisting of a compound of the formula VIII ##STR69## and an acid addition salt thereof, wherein n is 1 or 2, R a represents alkyl having 1-6 carbon atoms, R b represents alkyl having 1-6 carbon atoms, R c represents alkyl having 1-9 carbon atoms, phenyl, benzyl or phenylethyl, R d represents alkyl having 1-6 carbon atoms, or R c and R d together represent tetra- or pentamethylene, R e represents hydrogen, alkyl having 1-5 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms or aralkyl having 7-8 carbon atoms, R f represents hydrogen, alkyl having 1-5 carbon atoms, alkenyl having 3-4 carbon atoms or aralkyl having 7-8 carbon atoms, with R e and R f being mutually exchangeable, and X represents oxygen or --NR--, R represents hydrogen, alkyl having 1-18 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms, cycloalkyl having 5-12 carbon atoms, aryl having 6-10 carbon atoms, or aralkyl having 7-9 carbon atoms, R 1 represents hydrogen, --O; --OH, alkyl having 1-12 carbon atoms, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or a group of the formula --CH 2 --CH(OR 5 )--R 4 wherein R 4 represents hydrogen, methyl or phenyl, and R 5 represents hydrogen or a group A--CO--, or R 1 represents a group A--CO--, and in both cases A represents alkyl having 1-12 carbon atoms, alkenyl having 2 or 3 carbon atoms, cyclohexyl, phenyl, benzyl, a phenyl or phenylethyl group substituted by 2 alkyl groups each having 1-4 carbon atoms and a hydroxyl group, alkylamino having 1-12 carbon atoms, dialkylamino having 2-16 carbon atoms, anilino, alkoxy having 1-12 carbon atoms, benzyloxy or phenoxy, R 3 represents, in the case where n is 1, alkyl having 1-20 carbon atoms, or alkyl having 1-10 carbon atoms, which is substituted by one or more of the groups --OR 9 , --SR 10 , --CO--R 11 , --CN, --C(O)--YR 12 , --O--C(O)R 13 or --P(O)(OR 14 ) 2 , wherein R 9 denotes phenyl or alkylphenyl having 6-10 carbon atoms, benzyl or cyclohexyl, R 10 represents phenyl or alkylphenyl having 6-10 carbon atoms, R 11 denotes alkyl having 1-12 carbon atoms, Y represents --O-- or --NR-- wherein R is as previously defined, R 12 denotes alkyl having 1-18 carbon atoms, cycloalkyl having 5-12 carbon atoms, or a group of the formula IIIb ##STR70## wherein R 17 represents a group as defined for R', R13 denotes alkyl having 1-17 carbon atoms, cycloalkyl having 5-12 carbon atoms, or phenyl or phenylalkyl having 7-9 carbon atoms, wherein the phenyl radical is unsubstituted or is substituted by at least one of the groups alkyl having 1-4 carbon atoms and hydroxyl, and R 14 denotes alkyl having 1-8 carbon atoms, allyl or phenyl, and X has the above-defined meaning, and R 3 further represents an alkyl group having 2-22 carbon atoms, which is interrupted by --O--, --S--, --SO-- or --SO 2 --, alkenyl having 3-18 carbon atoms, alkynyl having 3-8 carbon atoms, cycloalkyl having 5-12 carbon atoms, alkyl-cycloalkyl having 6-18 carbon atoms, cycloalkyl-alkyl having 6-14 carbon atoms, aralkyl or alkyl-aralkyl having 7-19 carbon atoms, phenyl, or a group --OR 15 , wherein R 15 is alkyl having 1-18 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms, cycloalkyl having 5-12 carbon atoms or aralkyl having 7-9 carbon atoms, or R 3 represents a group --O--C(O)R 16 or --NH--C(O)R 16 , wherein R 16 is alkyl having 1-12 carbon atoms, alkenyl having 2 or 3 carbon atoms, cyclohexyl, phenyl, benzyl, a phenyl or phenylethyl group substituted by 2 alkyl groups each having 1- 4 carbon atoms and a hydroxyl group, or R 3 is a group of the formula III or of the formula IV ##STR71## wherein R 18 represents alkyl having 1-20 carbon atoms, allyl, benzyl, phenyl, cyclohexyl, alkoxyalkyl having 3-8 carbon atoms, or a group --O--C(O)R 16 or --NH--C(O)R 16 as defined above, or has one of the meanings given for R 2 , and R 19 and R 20 each independently represent alkyl having 1-6 carbon atoms, or a radical of the formula III, and, in addition, R 3 represents, in the case where n is 2, a direct bond, alkylene having 1-20 carbon atoms, alkylene having 2-20 carbon atoms, which is interrupted by one or two of the members --O--, --S--, --SO--, --SO 2 -- or --CO--O--, arylene-bis-alkylene having 8-14 carbon atoms, alkenylene having 4-8 carbon atoms, or alkynylene having 4-8 carbon atoms.
Claim 8
Dependent Claim
750 words
A member selected from the group consisting of a compound of the formula VIII ##STR69## and an acid addition salt thereof, wherein n is 1 or 2, R a represents alkyl having 1-6 carbon atoms, R b represents alkyl having 1-6 carbon atoms, R c represents alkyl having 1-9 carbon atoms, phenyl, benzyl or phenylethyl, R d represents alkyl having 1-6 carbon atoms, or R c and R d together represent tetra- or pentamethylene, R e represents hydrogen, alkyl having 1-5 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms or aralkyl having 7-8 carbon atoms, R f represents hydrogen, alkyl having 1-5 carbon atoms, alkenyl having 3-4 carbon atoms or aralkyl having 7-8 carbon atoms, with R e and R f being mutually exchangeable, and X represents oxygen or --NR--, R represents hydrogen, alkyl having 1-18 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms, cycloalkyl having 5-12 carbon atoms, aryl having 6-10 carbon atoms, or aralkyl having 7-9 carbon atoms, R 1 represents hydrogen, --O; --OH, alkyl having 1-12 carbon atoms, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or a group of the formula --CH 2 --CH(OR 5 )--R 4 wherein R 4 represents hydrogen, methyl or phenyl, and R 5 represents hydrogen or a group A--CO--, or R 1 represents a group A--CO--, and in both cases A represents alkyl having 1-12 carbon atoms, alkenyl having 2 or 3 carbon atoms, cyclohexyl, phenyl, benzyl, a phenyl or phenylethyl group substituted by 2 alkyl groups each having 1-4 carbon atoms and a hydroxyl group, alkylamino having 1-12 carbon atoms, dialkylamino having 2-16 carbon atoms, anilino, alkoxy having 1-12 carbon atoms, benzyloxy or phenoxy, R 3 represents, in the case where n is 1, alkyl having 1-20 carbon atoms, or alkyl having 1-10 carbon atoms, which is substituted by one or more of the groups --OR 9 , --SR 10 , --CO--R 11 , --CN, --C(O)--YR 12 , --O--C(O)R 13 or --P(O)(OR 14 ) 2 , wherein R 9 denotes phenyl or alkylphenyl having 6-10 carbon atoms, benzyl or cyclohexyl, R 10 represents phenyl or alkylphenyl having 6-10 carbon atoms, R 11 denotes alkyl having 1-12 carbon atoms, Y represents --O-- or --NR-- wherein R is as previously defined, R 12 denotes alkyl having 1-18 carbon atoms, cycloalkyl having 5-12 carbon atoms, or a group of the formula IIIb ##STR70## wherein R 17 represents a group as defined for R', R13 denotes alkyl having 1-17 carbon atoms, cycloalkyl having 5-12 carbon atoms, or phenyl or phenylalkyl having 7-9 carbon atoms, wherein the phenyl radical is unsubstituted or is substituted by at least one of the groups alkyl having 1-4 carbon atoms and hydroxyl, and R 14 denotes alkyl having 1-8 carbon atoms, allyl or phenyl, and X has the above-defined meaning, and R 3 further represents an alkyl group having 2-22 carbon atoms, which is interrupted by --O--, --S--, --SO-- or --SO 2 --, alkenyl having 3-18 carbon atoms, alkynyl having 3-8 carbon atoms, cycloalkyl having 5-12 carbon atoms, alkyl-cycloalkyl having 6-18 carbon atoms, cycloalkyl-alkyl having 6-14 carbon atoms, aralkyl or alkyl-aralkyl having 7-19 carbon atoms, phenyl, or a group --OR 15 , wherein R 15 is alkyl having 1-18 carbon atoms, alkenyl having 3-4 carbon atoms, alkynyl having 3-4 carbon atoms, cycloalkyl having 5-12 carbon atoms or aralkyl having 7-9 carbon atoms, or R 3 represents a group --O--C(O)R 16 or --NH--C(O)R 16 , wherein R 16 is alkyl having 1-12 carbon atoms, alkenyl having 2 or 3 carbon atoms, cyclohexyl, phenyl, benzyl, a phenyl or phenylethyl group substituted by 2 alkyl groups each having 1- 4 carbon atoms and a hydroxyl group, or R 3 is a group of the formula III or of the formula IV ##STR71## wherein R 18 represents alkyl having 1-20 carbon atoms, allyl, benzyl, phenyl, cyclohexyl, alkoxyalkyl having 3-8 carbon atoms, or a group --O--C(O)R 16 or --NH--C(O)R 16 as defined above, or has one of the meanings given for R 2 , and R 19 and R 20 each independently represent alkyl having 1-6 carbon atoms, or a radical of the formula III, and, in addition, R 3 represents, in the case where n is 2, a direct bond, alkylene having 1-20 carbon atoms, alkylene having 2-20 carbon atoms, which is interrupted by one or two of the members --O--, --S--, --SO--, --SO 2 -- or --CO--O--, arylene-bis-alkylene having 8-14 carbon atoms, alkenylene having 4-8 carbon atoms, or alkynylene having 4-8 carbon atoms.
Claim 9
Dependent Claim
12 words
A compound according to claim 1, said compound being butyl-(3,5-di-tert. butyl-4-hydroxybenzyl)-malonic acid-bis-(1,2,2,6,6-pentamethyl-4-piperidinyl)ester.
Claim 10
Dependent Claim
11 words
A compound according to claim 1, said compound being dodecyl-(3,5-di-tert.butyl-4-hydroxybenzyl)-malonic acid-bis-(1,2,2,6,6-pentamethyl-4-piperidinyl)ester.
Claim 11
Dependent Claim
11 words
A compound according to claim 1, said compound being 1,2,2,6,6-pentamethyl-4-piperidinyloxycarbonylmethyl-(3,5-di-tert.butyl-4-hydroxybenzyl)-malonic acid-bis-(1,2,2,6,6-pentamethyl-4-piperidinyl)ester.
Claim 12
Dependent Claim
11 words
A compound according to claim 1, said compound being butyl-(3,5-di-tert.butyl-4-hydroxybenzyl)-malonic acid-bis-(2,3,6-trimethyl-2,6-diethyl-4-piperidinyl)ester.
Claim 13
Dependent Claim
44 words
A method for stabilizing plastics to protect them from damage caused by the action of oxygen, heat and light, characterized in that 0.01 to 5 percent by weight of a compound or salt thereof according to claim 1 is added to the plastics material.
Claim 14
Dependent Claim
28 words
A method according to claim 10 characterized in that 0.05 to 1.5 percent by weight of a compound according to claim 2 is added to the plastics material.
Claim 15
Dependent Claim
28 words
A method according to claim 10 characterized in that 0.1 to 0.8 percent by weight of a compound according to claim 3 is added to the plastics material.
Claim 16
Dependent Claim
28 words
A method according to claim 10 characterized in that 0.01 to 5 percent by weight of a compound according to claim 4 is added to the plastics material.
Claim 17
Dependent Claim
37 words
A plastics material stabilized against damage caused by the action of oxygen, heat and light, which plastics material contains as stabilizer 0.01 to 5 percent by weight of a compound or salt thereof according to claim 1.
Claim 18
Dependent Claim
22 words
A stabilized plastics material according to claim 14 characterized in that the material is a polyolefin, a styrene polymer or a polyurethane.
Claim 19
Dependent Claim
27 words
A method for stabilizing plastics, characterized in that 0.01 to 5 percent by weight of a compound according to claim 5 is added to the plastics material.
Claim 20
Dependent Claim
18 words
A stabilized plastics material containing 0.01 to 5 percent by weight of a compound according to claim 5.
Claim 21
Dependent Claim
29 words
A compound according to claim 1 wherein R a and R c are ethyl; R b , R d and R e are methyl; and R f is hydrogen.
Claim 22
Dependent Claim
155 words
A compound according to claim 1 wherein n is 1 or 2; R a , R b , R c and R d are methyl and R e and R f are hydrogen, X is oxygen, R 1 is hydrogen, --O; alkyl having 1-4 carbon atoms, allyl or acetyl, R 2 is a hydroxybenzyl group of the formula (IIa) or (IIb), ##STR72## wherein R 6 represents tert. butyl, R 7 represents methyl or tert. butyl and R 8 represents hydrogen or methyl, and R 3 represents alkyl of 1-18 carbon atoms which is substituted by one or two groups of the formula --C(O)--OR 12 wherein R 12 represents alkyl of 1 to 4 carbon atoms or a group of the formula (IIIa) ##STR73## or a group --P(O)(OR 14 ) 2 , wherein R 13 represents alkyl of 1-4 carbon atoms or R 3 represents allyl, propargyl, benzyl, phenyl, alkylene having 1-8 carbon atoms or xylylene.
Claim 23
Dependent Claim
28 words
A compound according to claim 5 wherein R a , R b , R c and R d are methyl and R e and R f are hydrogen.
Claim 24
Dependent Claim
36 words
A plastics material stabilized against damage caused by the action of oxygen, heat and light, which plastics material contains as stabilizer 0.01 to 5% by weight of a compound or salt thereof according to claim 4.
References Cited (Backward Citations)
US4021432A
Cited
US3993655A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-04-15 | 1983-10-15 | 1984-04-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-04-15 | 1987-10-15 | 1988-04-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-04-15 | 1991-10-15 | 1992-04-15 | $7700.00 | Window Closed / Lapsed |