US4166814A
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Bis-polyalkylpiperidines
Assignee: BASF Corp
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Filing: 1977-10-11
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Granted: 1979-09-04
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Expires: 1997-10-11
Abstract
Abstract Polyalkylpiperidines of formula I, ##STR1## wherein R 1 is H or lower alkyl, R 2 is H, O or a monovalent organic residue and Z is a divalent aromatic residue, are excellent light stabilizers for plastics. These compounds can be prepared from the according 4-oxopiperidines by Wittig-Horner reaction with diphosphonates of the formula IV, (ro).sub.2 (o)p--ch.sub.2 --z--ch.sub.2 --p(o)(or).sub.2 iv wherein R denotes lower alkyl, and subsequent hydrogenation of the resulting diolefines. The compounds of formula I are especially suitable for the stabilization of polyolefins, styrene polymers and polyurethanes.
Inventors
- 👤 Friedrich Karrer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 00:28
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/68; C07D211/70; C07D211/06; C07D211/08; C07D211/18; C07D211/26; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
241 words
A compound of the formula I ##STR18## in which R 1 denotes hydrogen or alkyl with 1-4 C atoms, R 2 denotes hydrogen, an oxyl radical, alkyl with 1-12 C atoms, alkenyl with 3-6 C atoms, alkynyl with 3-6 C atoms, 2,3-epoxypropyl, aralkyl or alkaralkyl with 7-11 C atoms or one of the groups --CO--R 3 , --CH 2 COOR 4 , --COOR 4 , --CONHR 5 , --CH 2 CONHR 5 or --CH 2 CH(R 6 )OR 7 , R 3 denotes hydrogen, alkyl with 1-6 C atoms, alkenyl with 2-4 C atoms, alkynyl with 2-4 C atoms or aralkyl or alkaralkyl with 7-15 C atoms, R 4 denotes alkyl with 1-12 C atoms, alkenyl with 3-6 C atoms, aralkyl with 7-8 C atoms or cyclohexyl, R 5 denotes alkyl with 1-18 C atoms, aralkyl or alkaralkyl with 7-15 C atoms, phenyl or alkylphenyl with 6- 8 C atoms or cyclohexyl, R 6 denotes hydrogen, methyl or phenyl, R 7 denotes hydrogen or an alkanoyl, alkenoyl, aroyl or alkaroyl group with up to 18 C atoms and Z denotes a phenylene group or a group of the formula II ##STR19## in which Y represents a direct bond or one of the groups --CH 2 --, --C(CH 3 ) 2 -- or --O--, and the salts of such a compound of the formula I with inorganic or organic acids and complexes of a compound of the formula I with nickel compounds.
Claim 2
Dependent Claim
241 words
A compound of the formula I ##STR18## in which R 1 denotes hydrogen or alkyl with 1-4 C atoms, R 2 denotes hydrogen, an oxyl radical, alkyl with 1-12 C atoms, alkenyl with 3-6 C atoms, alkynyl with 3-6 C atoms, 2,3-epoxypropyl, aralkyl or alkaralkyl with 7-11 C atoms or one of the groups --CO--R 3 , --CH 2 COOR 4 , --COOR 4 , --CONHR 5 , --CH 2 CONHR 5 or --CH 2 CH(R 6 )OR 7 , R 3 denotes hydrogen, alkyl with 1-6 C atoms, alkenyl with 2-4 C atoms, alkynyl with 2-4 C atoms or aralkyl or alkaralkyl with 7-15 C atoms, R 4 denotes alkyl with 1-12 C atoms, alkenyl with 3-6 C atoms, aralkyl with 7-8 C atoms or cyclohexyl, R 5 denotes alkyl with 1-18 C atoms, aralkyl or alkaralkyl with 7-15 C atoms, phenyl or alkylphenyl with 6- 8 C atoms or cyclohexyl, R 6 denotes hydrogen, methyl or phenyl, R 7 denotes hydrogen or an alkanoyl, alkenoyl, aroyl or alkaroyl group with up to 18 C atoms and Z denotes a phenylene group or a group of the formula II ##STR19## in which Y represents a direct bond or one of the groups --CH 2 --, --C(CH 3 ) 2 -- or --O--, and the salts of such a compound of the formula I with inorganic or organic acids and complexes of a compound of the formula I with nickel compounds.
Claim 3
Dependent Claim
16 words
A compound according to claim 1, of the formula I, in which R 1 is hydrogen.
Claim 4
Dependent Claim
35 words
A compound according to claim 1, of the formula I, in which R 2 denotes hydrogen, alkyl with 1-6 C atoms, alkenyl with 3-5 C atoms, propargyl, benzyl, acetyl, propionyl, butyroyl, acryloyl, methacryloyl or crotonyl.
Claim 5
Dependent Claim
20 words
A compound according to claim 3, of the formula I, in which R 2 denotes hydrogen, methyl, allyl or benzyl.
Claim 6
Dependent Claim
17 words
A compound according to claim 1, of the formula I, in which Z denotes phenylene or para-diphenylene.
Claim 7
Dependent Claim
9 words
The compound according to claim 1, which is 1,4-Bis-(2,2,6,6-tetramethyl-piperidin-4-yl-methyl)-benzene.
Claim 8
Dependent Claim
9 words
The compound according to claim 1, which is 1,4-Bis-(1-methyl-2,2,6,6-tetramethyl-piperidin-4-yl-methyl)-benzene.
Claim 9
Dependent Claim
9 words
The compound according to claim 1, which is 1,4-Bis-(1-benzyl-2,2,6,6-tetramethyl-piperidin-4-yl-methyl)-benzene.
Claim 10
Dependent Claim
7 words
The compound according to claim 1, 1,4-Bis-(1-acetyl-2,2,6,6-tetramethyl-piperidin-4-yl-methyl)-benzene.
Claim 11
Dependent Claim
238 words
A compound of the formula VI ##STR20## wherein R 1 denotes hydrogen or alkyl with 1-4 C atoms, R 2 denotes hydrogen, an oxyl radical, alkyl with 1-12 C atoms, alkenyl with 3-6 C atoms, alkynyl with 3-6 C atoms, 2,3-epoxypropyl, aralkyl or alkaralkyl with 7-11 C atoms or one of the groups --CO--R 3 , --CH 2 COOR 4 , --COOR 4 , --CONHR 5 , --CH 2 CONHR 5 or --CH 2 CH(R 6 )OR 7 , R 3 denotes hydrogen, alkyl with 1-6 C atoms, alkenyl with 2-4 C atoms, alkynyl with 2-4 C atoms of aralkyl or alkaralkyl with 7-15 C atoms, R 4 denotes alkyl with 1-12 C atoms, alkenyl with 3-6 C atoms, aralkyl with 7-8 C atoms or cyclohexyl, R 5 denotes alkyl with 1-18 C atoms, aralkyl or alkaralkyl with 7-15 C atoms, phenyl or alkylphenyl with 6-8 C atoms of cyclohexyl, R 6 denotes hydrogen, methyl or phenyl, R 7 denotes hydrogen or an alkanoyl, aroyl or alkaroyl group with up to 18 C atoms and Z denotes a phenylene group or a group of the formula II ##STR21## in which Y represents a direct bond or one of the groups --CH 2 --, --C(CH 3 ) 2 -- or --O--, and the salts of such a compound of the formula I with inorganic or organic acids and complexes of a compound of the formula I with nickel compounds.
Claim 12
Dependent Claim
238 words
A compound of the formula VI ##STR20## wherein R 1 denotes hydrogen or alkyl with 1-4 C atoms, R 2 denotes hydrogen, an oxyl radical, alkyl with 1-12 C atoms, alkenyl with 3-6 C atoms, alkynyl with 3-6 C atoms, 2,3-epoxypropyl, aralkyl or alkaralkyl with 7-11 C atoms or one of the groups --CO--R 3 , --CH 2 COOR 4 , --COOR 4 , --CONHR 5 , --CH 2 CONHR 5 or --CH 2 CH(R 6 )OR 7 , R 3 denotes hydrogen, alkyl with 1-6 C atoms, alkenyl with 2-4 C atoms, alkynyl with 2-4 C atoms of aralkyl or alkaralkyl with 7-15 C atoms, R 4 denotes alkyl with 1-12 C atoms, alkenyl with 3-6 C atoms, aralkyl with 7-8 C atoms or cyclohexyl, R 5 denotes alkyl with 1-18 C atoms, aralkyl or alkaralkyl with 7-15 C atoms, phenyl or alkylphenyl with 6-8 C atoms of cyclohexyl, R 6 denotes hydrogen, methyl or phenyl, R 7 denotes hydrogen or an alkanoyl, aroyl or alkaroyl group with up to 18 C atoms and Z denotes a phenylene group or a group of the formula II ##STR21## in which Y represents a direct bond or one of the groups --CH 2 --, --C(CH 3 ) 2 -- or --O--, and the salts of such a compound of the formula I with inorganic or organic acids and complexes of a compound of the formula I with nickel compounds.
Claim 13
Dependent Claim
45 words
A compound according to claim 10, of the formula VI, in which R 1 denotes hydrogen, R 2 denotes hydrogen or methyl, Z denotes phenylene or a group of the formula II and Y denotes --CH 2 --, C(CH 3 ) 2 -- or --O--.
Claim 14
Dependent Claim
253 words
A plastic stabilised against degradation by light, which contains 0.01 to 5% by weight of a compound of the formula I ##STR22## wherein R 1 denotes hydrogen or alkyl with 1-4 C atoms, R 2 denotes hydrogen, an oxyl radical, alkyl with 1-12 C atoms, alkenyl with 3-5 C atoms, alkynyl with 3-5 C atoms, 2,3-epoxypropyl, aralkyl or alkaralkyl with 7-11 C atoms or one of the groups --CO--R 3 , --CH 2 COOR 4 , --COOR 4 , --CONHR 5 , --CH 2 CONHR 5 or --CH 2 CH(R 5 )OR 7 , R 3 denotes hydrogen, alkyl with 1-6 C atoms, alkenyl with 2-4 C atoms, alkynyl with 2-4 C atoms or aralkyl or alkaralkyl with 7-15 C atoms, R 4 denotes alkyl with 1-12 C atoms, alkenyl with 3-8 C atoms, aralkyl with 7-8 C atoms or cyclohexyl, R 5 denotes alkyl with 1-18 C atoms, aralkyl or alkaralkyl with 7-15 C atoms, phenyl or alkylphenyl with 6-8 C atoms or cyclohexyl, R 6 denotes hydrogen, methyl or phenyl, R 7 denotes hydrogen or an alkanoyl, aroyl or alkaroyl group with up to 18 C atoms and Z denotes a phenylene group or a group of the formula II ##STR23## in which Y represents a direct bond or one of the groups --CH 2 --, --C(CH 3 ) 2 -- or --O--, and the salts of such a compound of the formula I with inorganic or organic acids and complexes of a compound of the formula I with nickel compounds.
Claim 15
Dependent Claim
253 words
A plastic stabilised against degradation by light, which contains 0.01 to 5% by weight of a compound of the formula I ##STR22## wherein R 1 denotes hydrogen or alkyl with 1-4 C atoms, R 2 denotes hydrogen, an oxyl radical, alkyl with 1-12 C atoms, alkenyl with 3-5 C atoms, alkynyl with 3-5 C atoms, 2,3-epoxypropyl, aralkyl or alkaralkyl with 7-11 C atoms or one of the groups --CO--R 3 , --CH 2 COOR 4 , --COOR 4 , --CONHR 5 , --CH 2 CONHR 5 or --CH 2 CH(R 5 )OR 7 , R 3 denotes hydrogen, alkyl with 1-6 C atoms, alkenyl with 2-4 C atoms, alkynyl with 2-4 C atoms or aralkyl or alkaralkyl with 7-15 C atoms, R 4 denotes alkyl with 1-12 C atoms, alkenyl with 3-8 C atoms, aralkyl with 7-8 C atoms or cyclohexyl, R 5 denotes alkyl with 1-18 C atoms, aralkyl or alkaralkyl with 7-15 C atoms, phenyl or alkylphenyl with 6-8 C atoms or cyclohexyl, R 6 denotes hydrogen, methyl or phenyl, R 7 denotes hydrogen or an alkanoyl, aroyl or alkaroyl group with up to 18 C atoms and Z denotes a phenylene group or a group of the formula II ##STR23## in which Y represents a direct bond or one of the groups --CH 2 --, --C(CH 3 ) 2 -- or --O--, and the salts of such a compound of the formula I with inorganic or organic acids and complexes of a compound of the formula I with nickel compounds.
Claim 16
Dependent Claim
16 words
Stabilised plastic according to claim 12 wherein the plastic is a polyolefin, styrene polymer or polyurethane.
Claim 17
Dependent Claim
254 words
A plastic stabilised against degradation by light, which contains 0.01 to 5% by weight of a compound of the formula VI ##STR24## wherein R 1 denotes hydrogen or alkyl with 1-4 C atoms, R 2 denotes hydrogen, an oxyl radical, alkyl with 1-12 C atoms, alkenyl with 3-6 C atoms, alkynyl with 3-6 C atoms, 2,3-epoxypropyl, aralkyl or alkaralkyl with 7-11 C atoms or one of the groups --CO--R 3 , --CH 2 COOR 4 , --COOR 4 , --CONHR 5 , --CH 2 CONHR 5 or --CH 2 CH(R 6 )OR 7 , R 3 denotes hydrogen, alkyl with 1-6 C atoms, alkenyl with 2-4 C atoms, alkynyl with 2-4 C atoms or aralkyl or alkaralkyl with 7-15 C atoms, R 4 denotes alkyl with 1-12 C atoms, alkenyl with 3-5 C atoms, aralkyl with 7-8 C atoms or cyclohexyl, R 5 denotes alkyl with 1-18 C atoms, aralkyl or alkaralkyl with 7-15 C atoms, phenyl or alkylphenyl with 6-8 C atoms or cyclohexyl, R 6 denotes hydrogen, methyl or phenyl, R 7 denotes hydrogen or an alkanoyl, aroyl or alkaroyl group with up to 18 C atoms and 2 denotes a phenylene group or a group of the formula II ##STR25## in which Y represents a direct bond or one of the groups --CH 2 --, -- C(CH 3 ) 2 -- or --O--, and the salts of such a compound of the formula I with inorganic or organic acids and complexes of a compound of the formula I with nickel compounds.
Claim 18
Dependent Claim
254 words
A plastic stabilised against degradation by light, which contains 0.01 to 5% by weight of a compound of the formula VI ##STR24## wherein R 1 denotes hydrogen or alkyl with 1-4 C atoms, R 2 denotes hydrogen, an oxyl radical, alkyl with 1-12 C atoms, alkenyl with 3-6 C atoms, alkynyl with 3-6 C atoms, 2,3-epoxypropyl, aralkyl or alkaralkyl with 7-11 C atoms or one of the groups --CO--R 3 , --CH 2 COOR 4 , --COOR 4 , --CONHR 5 , --CH 2 CONHR 5 or --CH 2 CH(R 6 )OR 7 , R 3 denotes hydrogen, alkyl with 1-6 C atoms, alkenyl with 2-4 C atoms, alkynyl with 2-4 C atoms or aralkyl or alkaralkyl with 7-15 C atoms, R 4 denotes alkyl with 1-12 C atoms, alkenyl with 3-5 C atoms, aralkyl with 7-8 C atoms or cyclohexyl, R 5 denotes alkyl with 1-18 C atoms, aralkyl or alkaralkyl with 7-15 C atoms, phenyl or alkylphenyl with 6-8 C atoms or cyclohexyl, R 6 denotes hydrogen, methyl or phenyl, R 7 denotes hydrogen or an alkanoyl, aroyl or alkaroyl group with up to 18 C atoms and 2 denotes a phenylene group or a group of the formula II ##STR25## in which Y represents a direct bond or one of the groups --CH 2 --, -- C(CH 3 ) 2 -- or --O--, and the salts of such a compound of the formula I with inorganic or organic acids and complexes of a compound of the formula I with nickel compounds.
Claim 19
Dependent Claim
17 words
The stabilized plastic according to claim 14 wherein the plastic is a polyolefin, styrene polymer or polyurethane.
References Cited (Backward Citations)
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 |