US4166813A
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Polyalkylated 4-aminopiperidine derivatives
Assignee: Sankyo Co Ltd
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Filing: 1978-05-08
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Granted: 1979-09-04
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Expires: 1998-05-08
Abstract
Abstract New polyalkylated 4-aminopiperidine derivatives contain in their molecule two or three piperidine rings, each having two alkyl substituents at both the 2- and the 6- positions, optionally having substituents at the 1- and 3- positions and having an amino substituent at the 4- position. The piperidine rings are joined together by attachment of the 4-amino substituents through, where there are two piperidine rings, a polyalkylene, polyether or polyester chain, or through, where there are three piperidine rings, an isocyanurate or glycerol system. These compounds and their acid addition salts are useful as stabilizers for synthetic polymers.
Inventors
- 👤 Nobuo Soma
- 👤 Syoji Morimura
- 👤 Takao Yoshioka
- 👤 Tomoyuki Kurumada
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 03:01
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; C07D211/56; C07D211/58; C08L; C08L101/00
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
600 words
A compound of formula (I): ##STR383## wherein R 1 represents a hydrogen atom or a methyl group; R 2 represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, a cycloalkyl group having from 5 to 7 carbon atoms, an unsubstituted phenyl group, a phenyl group having one or more substituents selected from C 1 -C 4 alkyl and C 1 -C 4 alkoxy groups, a naphthyl group, an aralkyl group having 7 or 8 carbon atoms, an aliphatic, aromatic, araliphatic or alicyclic acyl group having up to 18 carbon atoms wherein the aryl moiety is unsubstituted or has one or more substituents selected from C 1 -C 4 alkyl and hydroxy groups, an alkylsulphonyl group having from 1 to 4 carbon atoms, a phenylsulphonyl group which is unsubstituted or has one or more C 1 -C 12 alkyl substituents, a group of formula --CONHR 3 wherein R 3 represents an alkyl group having from 1 to 18 carbon atoms, an unsubstituted phenyl group, a substituted phenyl group having one or more substituents selected from methyl groups, chlorine atoms and bromine atoms, a naphthyl group or a cycloalkyl group having from 5 to 7 carbon atoms, or a group of formula --CH 2 CH 2 OZ; when R 2 represents a hydrogen atom, Z of X and Y as defined herein below represents a hydrogen atom and when R 2 represents a group other than a hydrogen atom, Z represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an allyl group, a benzyl group, an aliphatic, aromatic, araliphatic or alicyclic acyl group having up to 18 carbon atoms wherein the aryl moiety is unsubstituted or has one or more substituents selected from C 1 -C 4 alkyl and hydroxy groups, or a group of formula --CONHR 9 wherein R 9 represents an alkyl group having from 1 to 18 carbon atoms, an unsubstituted phenyl group, a phenyl group having one or more substituents selected from methyl groups, chlorine atoms and bromine atoms, a naphthyl or a cycloalkyl group having from 5 to 7 carbon atoms; when R 2 represents a hydrogen atom, Y represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an alkenyl group having 3 or 4 carbon atoms or a benzyl group, and, when R 2 represents a group other than a hydrogen atom, Y represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an alkenyl group having 3 or 4 carbon atoms, a benzyl group, a 2,3-epoxypropyl group, an aliphatic acyl group having up to 18 carbon atoms or one of the groups of formulae ##STR384## wherein R 6 represents an alkyl group having from 1 to 4 carbon atoms; R 7 represents a hydrogen atom, a methyl group or a phenyl group; R 8 represents an alkyl group having from 1 to 18 carbon atoms; and Z is as defined above; b represents 2 or 3; and when b=2, X represents one of the groups of formulae ##STR385## m represents an integer of from 1 to 10; n represents an integer of from 1 to 10; R 4 represents a hydrogen atom or a methyl group; W represents one of the groups of formulae ##STR386## wherein p represents 0, 1 or 2; R 5 represents a halogen atom; q represents an integer of from 1 to 10; and Z is as defined above; when b=3, X represents one of the groups of formulae ##STR387## wherein Z is as defined above, and an acid addition salt thereof.
Claim 2
Dependent Claim
600 words
A compound of formula (I): ##STR383## wherein R 1 represents a hydrogen atom or a methyl group; R 2 represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, a cycloalkyl group having from 5 to 7 carbon atoms, an unsubstituted phenyl group, a phenyl group having one or more substituents selected from C 1 -C 4 alkyl and C 1 -C 4 alkoxy groups, a naphthyl group, an aralkyl group having 7 or 8 carbon atoms, an aliphatic, aromatic, araliphatic or alicyclic acyl group having up to 18 carbon atoms wherein the aryl moiety is unsubstituted or has one or more substituents selected from C 1 -C 4 alkyl and hydroxy groups, an alkylsulphonyl group having from 1 to 4 carbon atoms, a phenylsulphonyl group which is unsubstituted or has one or more C 1 -C 12 alkyl substituents, a group of formula --CONHR 3 wherein R 3 represents an alkyl group having from 1 to 18 carbon atoms, an unsubstituted phenyl group, a substituted phenyl group having one or more substituents selected from methyl groups, chlorine atoms and bromine atoms, a naphthyl group or a cycloalkyl group having from 5 to 7 carbon atoms, or a group of formula --CH 2 CH 2 OZ; when R 2 represents a hydrogen atom, Z of X and Y as defined herein below represents a hydrogen atom and when R 2 represents a group other than a hydrogen atom, Z represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an allyl group, a benzyl group, an aliphatic, aromatic, araliphatic or alicyclic acyl group having up to 18 carbon atoms wherein the aryl moiety is unsubstituted or has one or more substituents selected from C 1 -C 4 alkyl and hydroxy groups, or a group of formula --CONHR 9 wherein R 9 represents an alkyl group having from 1 to 18 carbon atoms, an unsubstituted phenyl group, a phenyl group having one or more substituents selected from methyl groups, chlorine atoms and bromine atoms, a naphthyl or a cycloalkyl group having from 5 to 7 carbon atoms; when R 2 represents a hydrogen atom, Y represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an alkenyl group having 3 or 4 carbon atoms or a benzyl group, and, when R 2 represents a group other than a hydrogen atom, Y represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an alkenyl group having 3 or 4 carbon atoms, a benzyl group, a 2,3-epoxypropyl group, an aliphatic acyl group having up to 18 carbon atoms or one of the groups of formulae ##STR384## wherein R 6 represents an alkyl group having from 1 to 4 carbon atoms; R 7 represents a hydrogen atom, a methyl group or a phenyl group; R 8 represents an alkyl group having from 1 to 18 carbon atoms; and Z is as defined above; b represents 2 or 3; and when b=2, X represents one of the groups of formulae ##STR385## m represents an integer of from 1 to 10; n represents an integer of from 1 to 10; R 4 represents a hydrogen atom or a methyl group; W represents one of the groups of formulae ##STR386## wherein p represents 0, 1 or 2; R 5 represents a halogen atom; q represents an integer of from 1 to 10; and Z is as defined above; when b=3, X represents one of the groups of formulae ##STR387## wherein Z is as defined above, and an acid addition salt thereof.
Claim 3
Dependent Claim
14 words
A compound as claimed in claim 1, wherein R 1 represents a hydrogen atom.
Claim 4
Dependent Claim
63 words
A compound as claimed in claim 1, wherein R 2 represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, a cyclohexyl group, an alkanoyl group having from 2 to 12 carbon atoms, a benzoyl group or a group of formula --CH 2 CH 2 OZ' wherein Z' represents a hydrogen atom, an acetyl group or a benzoyl group.
Claim 5
Dependent Claim
64 words
A compound as claimed in claim 1, wherein X represents a group of formula ##STR388## wherein W' represents one of the groups of formulae ##STR389## --CO[CH 2 ] q CO-- and --CH 2 CH 2 -- wherein q is an integer of from 1 to 10; Z' represents a hydrogen atom, an acetyl group or a benzoyl group, and n' is 0 or 1.
Claim 6
Dependent Claim
20 words
A compound as claimed in claim 4, wherein W' represents one of the groups of formulae ##STR390## n' represents 1.
Claim 7
Dependent Claim
23 words
A compound as claimed in claim 1, wherein Y represents a hydrogen atom, a methyl group, an allyl group or an acetyl group.
Claim 8
Dependent Claim
20 words
A compound as claimed in claim 1, wherein Z represents a hydrogen atom, an acetyl group or a benzoyl group.
Claim 9
Dependent Claim
66 words
A compound of formula (II): ##STR391## wherein R 12 represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms or a 2-hydroxyethyl group; X' represents a group of formula ##STR392## wherein W' represents one of the groups of formulae ##STR393## and --CH 2 CH 2 --, and n' represents 0 or 1; and Y' represents a hydrogen atom or a methyl group.
Claim 10
Dependent Claim
66 words
A compound of formula (II): ##STR391## wherein R 12 represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms or a 2-hydroxyethyl group; X' represents a group of formula ##STR392## wherein W' represents one of the groups of formulae ##STR393## and --CH 2 CH 2 --, and n' represents 0 or 1; and Y' represents a hydrogen atom or a methyl group.
Claim 11
Dependent Claim
623 words
A polymeric composition stabilized against photo- and thermal deterioration comprising a synthetic polymer and a stabilizing amount of stabilizer selected from the group consisting of compounds of formula (I): ##STR394## wherein R 1 represents a hydrogen atom or a methyl group; R 2 represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, a cycloalkyl group having from 5 to 7 carbon atoms, an unsubstituted phenyl group, a phenyl group having one or more substituents selected from C 1 -C 4 alkyl and C 1 -C 4 alkoxy groups, a naphthyl group, an aralkyl group having 7 or 8 carbon atoms, an aliphatic, aromatic, araliphatic or alicyclic acyl group having up to 18 carbon atoms wherein the aryl moiety is unsubstituted or has one or more substituents selected from C 1 -C 4 alkyl and hydroxy groups, an alkylsulphonyl group having from 1 to 4 carbon atoms, a phenylsulphonyl group which is unsubstituted or has one or more C 1 -C 12 alkyl substituents, a group of formula --CONHR 3 wherein R 3 represents an alkyl group having from 1 to 18 carbon atoms, an unsubstituted phenyl group, a substituted phenyl group having one or more substituents selected from methyl groups, chlorine atoms and bromine atoms, a naphthyl group or a cycloalkyl group having from 5 to 7 carbon atoms, or a group of formula --CH 2 CH 2 OZ; when R 2 represents a hydrogen atom, Z of X and Y as defined herein below represents a hydrogen atom and when R 2 represents a group other than a hydrogen atom, Z represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an allyl group, a benzyl group, an aliphatic, aromatic, araliphatic or alicyclic acyl group having up to 18 carbon atoms wherein the aryl moiety is unsubstituted or has one or more substituents selected from C 1 -C 4 alkyl and hydroxy groups, or a group of formula --CONHR 9 wherein R 9 represents an alkyl group having from 1 to 18 carbon atoms, an unsubstituted phenyl group, a phenyl group having one or more substituents selected from methyl groups, chlorine atoms and bromine atoms, a naphthyl or a cycloalkyl group having from 5 to 7 carbon atoms; when R 2 represents a hydrogen atom, Y represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an alkenyl group having 3 or 4 carbon atoms or a benzyl group, and, when R 2 represents a group other than a hydrogen atom, Y represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an alkenyl group having 3 or 4 carbon atoms, a benzyl group, a 2,3-epoxypropyl group, an aliphatic acyl group having up to 18 carbon atoms or one of the groups of formulae ##STR395## wherein R 6 represents an alkyl group having from 1 to 4 carbon atoms; R 7 represents a hydrogen atom, a methyl group or a phenyl group; R 8 represents an alkyl group having from 1 to 18 carbon atoms; and Z is as defined above; b represents 2 or 3; and when b=2, X represents one of the groups of formulae ##STR396## m represents an integer of from 1 to 10; n represents an integer of from 1 to 10; R 4 represents a hydrogen atom or a methyl group; W represents one of the groups of formulae ##STR397## wherein p represents 0, 1 or 2; R 5 represents a halogen atom; q represents an integer of from 1 to 10; and Z is as defined above; when b=3; X represents one of the groups of formulae ##STR398## wherein Z is as defined above, and acid addition salts thereof.
Claim 12
Dependent Claim
623 words
A polymeric composition stabilized against photo- and thermal deterioration comprising a synthetic polymer and a stabilizing amount of stabilizer selected from the group consisting of compounds of formula (I): ##STR394## wherein R 1 represents a hydrogen atom or a methyl group; R 2 represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, a cycloalkyl group having from 5 to 7 carbon atoms, an unsubstituted phenyl group, a phenyl group having one or more substituents selected from C 1 -C 4 alkyl and C 1 -C 4 alkoxy groups, a naphthyl group, an aralkyl group having 7 or 8 carbon atoms, an aliphatic, aromatic, araliphatic or alicyclic acyl group having up to 18 carbon atoms wherein the aryl moiety is unsubstituted or has one or more substituents selected from C 1 -C 4 alkyl and hydroxy groups, an alkylsulphonyl group having from 1 to 4 carbon atoms, a phenylsulphonyl group which is unsubstituted or has one or more C 1 -C 12 alkyl substituents, a group of formula --CONHR 3 wherein R 3 represents an alkyl group having from 1 to 18 carbon atoms, an unsubstituted phenyl group, a substituted phenyl group having one or more substituents selected from methyl groups, chlorine atoms and bromine atoms, a naphthyl group or a cycloalkyl group having from 5 to 7 carbon atoms, or a group of formula --CH 2 CH 2 OZ; when R 2 represents a hydrogen atom, Z of X and Y as defined herein below represents a hydrogen atom and when R 2 represents a group other than a hydrogen atom, Z represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an allyl group, a benzyl group, an aliphatic, aromatic, araliphatic or alicyclic acyl group having up to 18 carbon atoms wherein the aryl moiety is unsubstituted or has one or more substituents selected from C 1 -C 4 alkyl and hydroxy groups, or a group of formula --CONHR 9 wherein R 9 represents an alkyl group having from 1 to 18 carbon atoms, an unsubstituted phenyl group, a phenyl group having one or more substituents selected from methyl groups, chlorine atoms and bromine atoms, a naphthyl or a cycloalkyl group having from 5 to 7 carbon atoms; when R 2 represents a hydrogen atom, Y represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an alkenyl group having 3 or 4 carbon atoms or a benzyl group, and, when R 2 represents a group other than a hydrogen atom, Y represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an alkenyl group having 3 or 4 carbon atoms, a benzyl group, a 2,3-epoxypropyl group, an aliphatic acyl group having up to 18 carbon atoms or one of the groups of formulae ##STR395## wherein R 6 represents an alkyl group having from 1 to 4 carbon atoms; R 7 represents a hydrogen atom, a methyl group or a phenyl group; R 8 represents an alkyl group having from 1 to 18 carbon atoms; and Z is as defined above; b represents 2 or 3; and when b=2, X represents one of the groups of formulae ##STR396## m represents an integer of from 1 to 10; n represents an integer of from 1 to 10; R 4 represents a hydrogen atom or a methyl group; W represents one of the groups of formulae ##STR397## wherein p represents 0, 1 or 2; R 5 represents a halogen atom; q represents an integer of from 1 to 10; and Z is as defined above; when b=3; X represents one of the groups of formulae ##STR398## wherein Z is as defined above, and acid addition salts thereof.
Claim 13
Dependent Claim
14 words
A composition as claimed in claim 9, wherein R 1 represents a hydrogen atom.
Claim 14
Dependent Claim
63 words
A composition as claimed in claim 9, wherein R 2 represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, a cyclohexyl group, an alkanoyl group having from 2 to 12 carbon atoms, a benzoyl group or a group of formula --CH 2 CH 2 OZ' wherein Z' represents a hydrogen atom, an acetyl group or a benzoyl group.
Claim 15
Dependent Claim
64 words
A composition as claimed in claim 9, wherein X represents a group of formula ##STR399## wherein W' represents one of the groups of formulae ##STR400## --CO[CH 2 ] q CO-- and --CH 2 CH 2 -- wherein q is an integer of from 1 to 10; Z' represents a hydrogen atom, an acetyl group or a benzoyl group, and n' is 0 or 1.
Claim 16
Dependent Claim
20 words
A composition as claimed in claim 12, wherein W' represents one of the groups of formulae ##STR401## n' represents 1.
Claim 17
Dependent Claim
23 words
A composition as claimed in claim 9, wherein Y represents a hydrogen atom, a methyl group, an allyl group or an acetyl group.
Claim 18
Dependent Claim
20 words
A composition as claimed in claim 9, wherein Z represents a hydrogen atom, an acetyl group or a benzoyl group.
Claim 19
Dependent Claim
78 words
A composition as claimed in claim 9, wherein said stabilizer is selected from compounds of formula (II): ##STR402## wherein R 12 represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms or a 2-hydroxyethyl group; X' represents a group of formula ##STR403## wherein W' represents one of the groups of formulae ##STR404## and --CH 2 CH 2 --, and n' represents 0 or 1; and Y' represents a hydrogen atom or a methyl group.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-09-03 | 1983-03-05 | 1983-09-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-09-03 | 1987-03-05 | 1987-09-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-09-03 | 1991-03-05 | 1991-09-04 | $7700.00 | Window Closed / Lapsed |