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US4148783A Expired / Lapsed US ⏱️ 0.0 years remaining

Hydroxybenzylmalonic acid derivatives

Assignee: BASF Corp
•
Filing: 1976-12-06
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Granted: 1979-04-10
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Expires: 1996-12-06
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Abstract

Abstract Hydroxybenzylmalonic acid derivatives of 1-acylpiperidin-4-ols or 1-acyl-4-aminopiperidines respectively having the formula ##STR1## WHEREIN R a , R b , R c , R d are hydrocarbon residues, R e is H or lower alkyl, R 1 is a hydroxybenzyl residue, R 2 is H or R 1 , X is --O-- or --NH-- and Y is hydrogen, a hydrocarbon, amino, alkoxy or phenoxy residue are excellent stabilizers for plastics material, especially for polyolefins. They act against heat aging as well as against light aging. The compounds may be prepared by acylation of the corresponding NH compounds or by hydroxybenzylation of the corresponding malonic acid derivatives.

Inventors

  • 👤 Michael Rasberger
  • 👤 Jean Rody
  • 👤 Francois Gugumus

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 17:46
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 211 words
A compound of the formula I, ##STR14## wherein X can be oxygen or --NH--, R 1 represents a hydroxybenzyl group of the formula II ##STR15## wherein R 3 and R 4 each independently represent an alkyl group having 1-9 C-atoms, aralkyl having 7-9 C-atoms or cycloalkyl having 5-8 C-atoms, and R 5 represents hydrogen or methyl, R 2 represents, in the case where X is oxygen, hydrogen or a hydroxybenzyl group of the formula II, in the case however where X is --NH--only hydrogen, Y represents hydrogen, alkyl having 1-17 C-atoms, alkenyl having 2-3 C-atoms, cyclohexyl, phenyl, benzyl, a phenyl or phenylethyl group substituted by 2 alkyl groups each having 1-4 C-atoms and a hydroxyl group, alkylamino having 1-12 C-atoms, dialkylamino having 2-16 C-atoms, anilino, alkoxy having 1-12 C-atoms, benzyloxy or phenoxy, R a represents methyl, R b represents alkyl having 1-6 C-atoms, R c represents alkyl having 1-9 C-atoms, phenyl, benzyl or phenylethyl, R d represents alkyl having 1-6 C-atoms, or R c and R d together with the C-atom to which they are bound form a cyclopentane or cyclohexane ring, and R e represents hydrogen or alkyl having 1-5 C-atoms, with the number of the C-atoms of R e being less by 1 than that of R b .
Claim 2
Dependent Claim 211 words
A compound of the formula I, ##STR14## wherein X can be oxygen or --NH--, R 1 represents a hydroxybenzyl group of the formula II ##STR15## wherein R 3 and R 4 each independently represent an alkyl group having 1-9 C-atoms, aralkyl having 7-9 C-atoms or cycloalkyl having 5-8 C-atoms, and R 5 represents hydrogen or methyl, R 2 represents, in the case where X is oxygen, hydrogen or a hydroxybenzyl group of the formula II, in the case however where X is --NH--only hydrogen, Y represents hydrogen, alkyl having 1-17 C-atoms, alkenyl having 2-3 C-atoms, cyclohexyl, phenyl, benzyl, a phenyl or phenylethyl group substituted by 2 alkyl groups each having 1-4 C-atoms and a hydroxyl group, alkylamino having 1-12 C-atoms, dialkylamino having 2-16 C-atoms, anilino, alkoxy having 1-12 C-atoms, benzyloxy or phenoxy, R a represents methyl, R b represents alkyl having 1-6 C-atoms, R c represents alkyl having 1-9 C-atoms, phenyl, benzyl or phenylethyl, R d represents alkyl having 1-6 C-atoms, or R c and R d together with the C-atom to which they are bound form a cyclopentane or cyclohexane ring, and R e represents hydrogen or alkyl having 1-5 C-atoms, with the number of the C-atoms of R e being less by 1 than that of R b .
Claim 3
Dependent Claim 82 words
A compound according to claim 1 of the formula I wherein R 1 represents a hydroxybenzyl group of the formula IIa ##STR16## R 2 is hydrogen, or, in the case where X is --O--, can also be identical to R 1 , R 3 represents an isopropyl, tert.butyl or tert.amyl group, R 4 represents a methyl, ethyl, isopropyl, tert.butyl, tert.amyl or tert.octyl group, and R 5 represents hydrogen or methyl, and Y represents alkyl having 1-4 C-atoms or alkenyl having 2-3 C-atoms.
Claim 4
Dependent Claim 33 words
A compound according to claim 2 of the formula I wherein R 3 represents tert.butyl, R 4 represents methyl or tert.butyl, R 5 represents hydrogen, and Y represents methyl, ethyl, vinyl or propenyl.
Claim 5
Dependent Claim 61 words
A compound according to claim 1 of the formula I wherein R 1 is a hydroxybenzyl group of the formula IIb, ##STR17## R 2 is hydrogen, or, in the case where X is --O--, can also be identical to R 1 , R 3 represents tert.butyl, tert.amyl or tert.octyl, and Y represents alkyl having 1-4 C-atoms or alkenyl having 2-3 C-atoms.
Claim 6
Dependent Claim 29 words
A compound according to claim 1, of the formula I wherein R a , R c and R e are methyl, and R b and R d are ethyl.
Claim 7
Dependent Claim 35 words
A compound according to claim 1, of the formula I wherein R a , R b and R c are methyl, R e is hydrogen, and R d is alkyl having 1-6 C-atoms or phenyl.
Claim 8
Dependent Claim 29 words
A compound according to claim 1, of the formula I wherein R a , R b , R c and R d are methyl, and R e is hydrogen.
Claim 9
Dependent Claim 28 words
Process for the stabilisation of plastics, against thermal-oxidative ageing and light-induced ageing, which process comprises the use of a compound of the formula I according to claim 1.
Claim 10
Dependent Claim 27 words
Plastics material stabilised against thermal-oxidative ageing and light-induced ageing, which material contains 0.01-5 percent by weight of a compound of the formula I according to claim 1.
Claim 11
Dependent Claim 27 words
Stabilised plastics material according to claim 9, which material contains 0.03-1.5, preferably 0.2-0.6, percent by weight of a compound of the formula I according to claim 1.
Claim 12
Dependent Claim 18 words
Stabilised plastics material according to claim 9, which material contains, in addition, other stabilisers or other usual additives.
Claim 13
Dependent Claim 7 words
The compound of claim 1, bis(3,5-di-tert.butyl-4-hydroxybenzyl)-malonic acid-bis(1-acetyl-2,2,6,6-tetramethyl-4-piperidinyl)ester.

References Cited (Backward Citations)

US3640928A Cited
US4021432A Cited
US3993655A Cited
US4075165A Cited
US4069196A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-04-09 1982-10-09 1983-04-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-04-09 1986-10-09 1987-04-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-04-09 1990-10-09 1991-04-10 $7700.00 Window Closed / Lapsed

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