US4293468A
Expired / Lapsed
US
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Malonate derivatives as stabilizers for organic materials
Assignee: BASF Corp
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Filing: 1980-02-04
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Granted: 1981-10-06
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Expires: 2000-02-04
Abstract
Abstract Malonates of the formula I ##STR1## in which R 1 is hydrogen or C 1 -C 4 -alkyl, R 2 is C 1 -C 12 -alkyl, C 3 -C 4 -alkenyl, benzyl or phenyl which is optionally substituted by C 1 -C 8 -alkyl or C 1 -C 8 -alkoxy, or is cyano, R 3 is C 1 -C 12 -alkyl, C 3 -C 4 -alkenyl or benzyl and X denotes 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 with 1-4 C atoms or one of the groups --CH 2 COOR 4 , --CH 2 --CH(R 5 )--OR 6 , --COOR 7 or --CONHR 7 , in which R 4 is C 1 -C 8 -alkyl, C 3 -C 6 -alkenyl, phenyl, C 7 -C 8 -aralkyl or cyclohexyl and R 5 is hydrogen, methyl or phenyl and R 6 denotes hydrogen or an aliphatic or aromatic, araliphatic or alicyclic acyl group with 1-18 C atoms, in which the aromatic part can optionally be substituted by chlorine, C 1 -C 4 -alkyl or C 1 -C 8 -alkoxy and/or by hydroxyl, and R 7 is C 1 -C 12 -alkyl, cyclohexyl, phenyl or benzyl as stabilizer for organic polymers.
Inventors
- 👤 Jean Rody
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 21:51
CPC Classifications
C; C09; C09K; C09K15/00; C09K15/04; C09K15/30; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
192 words
A malonate of the formula I ##STR4## in which R 1 is hydrogen or C 1 -C 4 -alkyl, R 2 is C 3 -C 4 -alkenyl, benzyl or phenyl, cyano or phenyl substituted by C 1 -C 8 -alkyl or C 1 -C 8 -alkoxy, R 3 is C 3 -C 4 -alkenyl or benzyl and X denotes 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 11 -aralkyl, 2,3-epoxypropyl, an aliphatic acyl group selected from formyl, acetyl, acryloyl or crotonyl, or one of the groups --CH 2 COOR 4 , --CH 2 --CH(R 5 )--OR 6 , --COOR 7 or --CONHR 7 , in which R 4 is C 1 -C 8 -alkyl, C 3 -C 6 -alkenyl, phenyl, C 7 -C 8 -aralkyl or cyclohexyl and R 5 is hydrogen, methyl or phenyl and R 6 denotes hydrogen or acetyl, propionyl, butyryl, octanoyl, dodecanoyl, stearoyl, acryloyl, benzoyl, chlorobenzoyl, toluoyl, isopropylbenzoyl, 2,4-dichlorobenzoyl, 4-methoxybenzoyl, 3-butoxybenzoyl, 2-hydroxybenzoyl, 3,5-di-t-butyl-4-hydroxybenzoyl, β-(3,5-di-t-butyl-4-hydroxyphenyl)propionyl, phenylacetyl, cinnamoyl or hexahydrobenzoyl and R 7 is C 1 -C 12 -alkyl, cyclohexyl, phenyl or benzyl.
Claim 2
Dependent Claim
192 words
A malonate of the formula I ##STR4## in which R 1 is hydrogen or C 1 -C 4 -alkyl, R 2 is C 3 -C 4 -alkenyl, benzyl or phenyl, cyano or phenyl substituted by C 1 -C 8 -alkyl or C 1 -C 8 -alkoxy, R 3 is C 3 -C 4 -alkenyl or benzyl and X denotes 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 11 -aralkyl, 2,3-epoxypropyl, an aliphatic acyl group selected from formyl, acetyl, acryloyl or crotonyl, or one of the groups --CH 2 COOR 4 , --CH 2 --CH(R 5 )--OR 6 , --COOR 7 or --CONHR 7 , in which R 4 is C 1 -C 8 -alkyl, C 3 -C 6 -alkenyl, phenyl, C 7 -C 8 -aralkyl or cyclohexyl and R 5 is hydrogen, methyl or phenyl and R 6 denotes hydrogen or acetyl, propionyl, butyryl, octanoyl, dodecanoyl, stearoyl, acryloyl, benzoyl, chlorobenzoyl, toluoyl, isopropylbenzoyl, 2,4-dichlorobenzoyl, 4-methoxybenzoyl, 3-butoxybenzoyl, 2-hydroxybenzoyl, 3,5-di-t-butyl-4-hydroxybenzoyl, β-(3,5-di-t-butyl-4-hydroxyphenyl)propionyl, phenylacetyl, cinnamoyl or hexahydrobenzoyl and R 7 is C 1 -C 12 -alkyl, cyclohexyl, phenyl or benzyl.
Claim 3
Dependent Claim
136 words
A malonate according to claim 1, of the formula (I), in which R 1 is hydrogen or methyl, R 2 is allyl, methallyl, benzyl or phenyl, R 3 is allyl, methallyl or benzyl and X is hydrogen, oxyl, C 1 -C 8 -alkyl, C 3 -C 4 -alkenyl or alkinyl, C 2 -C 6 -alkoxyalkyl, C 7 -C 11 -aralkyl, acetyl, acryloyl or crotonyl or denotes one of the groups --CH 2 --COOR 4 , --CH 2 --CH(R 5 ) --OR 6 , --COOR 7 or --CONHR 7 , in which R 4 is C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl, phenyl, C 7 -C 8 -aralkyl or cyclohexyl, R 5 is hydrogen, methyl or phenyl, R 6 is as defined in claim 15 and R 7 is C 1 -C 12 -alkyl.
Claim 4
Dependent Claim
102 words
A malonate according to claim 1, of the formula (I), in which R 1 is hydrogen or methyl, R 2 is allyl, methallyl, benzyl or phenyl, R 3 is benzyl and X is hydrogen, C 1 -C 4 -alkyl, allyl, benzyl, C 2 -C 6 -alkoxyalkyl, acetyl, acryloyl or crotonyl or one of the groups --CH 2 --COOR 4 , --CH 2 --CH(R 5 )--OR 6 , --COOR 7 or --CONHR 7 , in which R 4 is C 1 -C 4 -alkyl, R 5 denotes hydrogen or methyl, R 6 denotes hydrogen and R 7 is C 1 -C 4 -alkyl.
Claim 5
Dependent Claim
38 words
A malonate according to claim 1, of the formula (I), in which R 1 is hydrogen or methyl, R 2 is allyl, methallyl or benzyl, R 3 is benzyl and X is hydrogen, methyl, allyl, benzyl or acetyl.
Claim 6
Dependent Claim
18 words
A malonate according to claim 2, in which X is benzyl substituted by C 1 -C 4 -alkyl.
Claim 7
Dependent Claim
9 words
A malonate according to claim 1, namely bis-(1,2,2,6,6-pentamethyl-4-piperidinyl) dibenzylmalonate.
Claim 8
Dependent Claim
9 words
A malonate according to claim 1, namely bis-(1,2,2,6,6-pentamethyl-4-piperidinyl) diallylmalonate.
Claim 9
Dependent Claim
9 words
A malonate according to claim 1, namely bis-(1-allyl-2,2,6,6-tetramethyl-4-piperidinyl) dibenzylmalonate.
Claim 10
Dependent Claim
26 words
An organic material ordinarily subject to light- or thermal-induced degradation containing a malonate of claim 1 in amounts sufficient to stabilize the material against said degradation.
Claim 11
Dependent Claim
31 words
An organic material according to claim 9, wherein the malonate is present in amounts of from 0.01 to 5% by weight, based on the weight of the material to be stabilized.
Claim 12
Dependent Claim
14 words
An organic material according to claim 9, wherein the organic material is a polymer.
Claim 13
Dependent Claim
25 words
An organic material according to claim 11, wherein the polymer is selected from the group consisting of a polyolefin, a styrene or a polyurethane polymer.
Claim 14
Dependent Claim
34 words
A method of stabilizing an organic material ordinarily subject to light- and thermal-induced degradation which comprises adding to the organic material a stabilizing amount of a malonate of claim 1 to prevent said degradation.
Claim 15
Dependent Claim
31 words
A method according to claim 13, wherein the malonate is added in an amount of 0.01 to 5% by weight, based on the weight of the organic material to be stabilized.
Claim 16
Dependent Claim
13 words
A method according to claim 13, wherein the organic material is a polymer.
Claim 17
Dependent Claim
24 words
A method according to claim 15, wherein the polymer is selected from the group consisting of a polyolefin, a styrene of a polyurethane polymer.
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) | 1984-10-05 | 1985-04-06 | 1985-10-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-05 | 1989-04-06 | 1989-10-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-05 | 1993-04-06 | 1993-10-06 | $7700.00 | Window Closed / Lapsed |