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US3984460A Expired / Lapsed US ⏱️ 0.0 years remaining

Esters of trisubstituted hydroxyphenylalkanoic acids

Assignee: Novartis Corp
•
Filing: 1974-07-23
•
Granted: 1976-10-05
•
Expires: 1994-07-23
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Abstract

Abstract The compounds are esters and amides of trialkylhydroxyphenylalkanoic acid having the formula ##SPC1## Wherein R, R 1 and R 2 are independently lower alkyl or cycloalkyl groups, R 3 is hydrogen, alkyl, cycloalkyl, alkylene, phenyl, phenyl substituted by alkyl groups, alkylthioethyl, thiobis-alkylene, alkyleneoxyalkylene, polyoxyalkylene or a polyvalent cyclic or acyclic hydrocarbon radical, R 4 is hydrogen, lower alkyl, cycloalkyl, R 5 is hydrogen, alkyl, phenyl, phenyl substituted with alkyl groups, alkylene, polyoxyalkylene or polyvalent cyclic or acyclic hydrocarbon radical, A is lower alkylene, m is 1 to 4 and n is 1 to 6. The ester compounds of this invention are prepared via usual esterification procedures from a suitable alcohol and an acid of the formula I ##SPC2## or an acid halide or acid anhydride thereof. The higher alkyl esters can also be prepared from the lower alkyl ester, especially the methyl ester of the above represented compounds, by transesterification with a higher alkanol. The amide compounds of this invention are prepared by usual amidation procedures by reacting a carboxylic acid of formula I or an acid chloride or anhydride or a lower alkyl ester thereof with the appropriate amine. The compounds are useful as stabilizers for organic materials, especially polyolefins, which deteriorate upon exposure to light and heat.

Inventors

  • 👤 John d. Spivack

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 23:28
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/20; C08K5/04; C08K5/13; C08K5/134; C08K5/1345; C10; C10M; C10M2207/00; C10M2207/10; C10M2207/12; C10M2207/121; C10M2207/124; C10M2207/125; C10M2207/128; C10M2207/28; C10M2207/282; C10M2207/283; C10M2207/287; C10M2207/34; C10M2207/40; C10M2207/402; C10M2207/404; C10M2209/00; C10M2209/10; C10M2209/103; C10M2209/104; C10M2209/109; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/042; C10M2215/08; C10M2215/082; C10M2215/22; C10M2215/221; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/26; C10M2215/28; C10M2215/30; C10M2217/00; C10M2217/04; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/08; C10M2219/082; C10M2219/084; C10M2219/085; C10M2221/00; C10M2221/04; C10M2221/043; C10N; C10N2040/00; C10N2040/20; C10N2040/22

Claims Analysis

Total Claims: 47
Claim 1
Independent Claim 120 words
A compound having the formula ##SPC13## wherein R is a branched alkyl of 3 to 8 carbon atoms, R 1 and R 2 are alkyl of 1 to 3 carbon atoms or together are a butylene chain which together with the phenyl ring form a tetrahydronaphthyl group, R 3 is alkyl of 1 to 18 carbon atoms; cyclohexyl; phenyl; o-tolyl; p-tert-octylphenyl; 2,4-di-tert-butylphenyl; 2-(alkylthio)ethyl of 5 to 21 atoms in the chain; alkylene of 2 to 6 carbon atoms, thiodiethylene, 3,6-dioxa-1,8-octamethylene; or a polyvalent saturated aliphatic hydrocarbon radical of 3 to 7 carbon atoms where n is 3 or 4, A is a straight chain alkylene of 1 to 3 carbon atoms, and n is an integer of 1 to 4.
Claim 2
Dependent Claim 120 words
A compound having the formula ##SPC13## wherein R is a branched alkyl of 3 to 8 carbon atoms, R 1 and R 2 are alkyl of 1 to 3 carbon atoms or together are a butylene chain which together with the phenyl ring form a tetrahydronaphthyl group, R 3 is alkyl of 1 to 18 carbon atoms; cyclohexyl; phenyl; o-tolyl; p-tert-octylphenyl; 2,4-di-tert-butylphenyl; 2-(alkylthio)ethyl of 5 to 21 atoms in the chain; alkylene of 2 to 6 carbon atoms, thiodiethylene, 3,6-dioxa-1,8-octamethylene; or a polyvalent saturated aliphatic hydrocarbon radical of 3 to 7 carbon atoms where n is 3 or 4, A is a straight chain alkylene of 1 to 3 carbon atoms, and n is an integer of 1 to 4.
Claim 3
Dependent Claim 22 words
A compound of claim 1 wherein R is a branched chain alkyl and R 1 and R 2 are straight chain alkyl.
Claim 4
Dependent Claim 10 words
A compound of claim 2 wherein R 3 is alkyl.
Claim 5
Dependent Claim 10 words
A compound of claim 2 wherein R 3 is 2-(alkylthio)ethyl.
Claim 6
Dependent Claim 17 words
A compound of claim 3 wherein R is tert-alkyl and R 1 and R 2 are methyl.
Claim 7
Dependent Claim 17 words
A compound of claim 4 wherein R is tert-alkyl and R 1 and R 2 are methyl.
Claim 8
Dependent Claim 10 words
A compound of claim 2 wherein R 3 is alkylene.
Claim 9
Dependent Claim 14 words
A compound of claim 2 wherein R 3 is polyvalent saturated aliphatic hydrocarbon radical.
Claim 10
Dependent Claim 10 words
A compound of claim 2 wherein R 3 is thiodiethylene.
Claim 11
Dependent Claim 10 words
A compound of claim 2 wherein R 3 is 3,6-dioxa-1,8-octamethylene.
Claim 12
Dependent Claim 17 words
A compound of claim 7 wherein R is tert-alkyl and R 1 and R 2 are methyl.
Claim 13
Dependent Claim 17 words
A compound of claim 8 wherein R is tert-alkyl and R 1 and R 2 are methyl.
Claim 14
Dependent Claim 17 words
A compound of claim 9 wherein R is tert-alkyl and R 1 and R 2 are methyl.
Claim 15
Dependent Claim 17 words
A compound of claim 10 wherein R is tert-alkyl and R 1 and R 2 are methyl.
Claim 16
Dependent Claim 7 words
The compound of claim 1, methyl 3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate.
Claim 17
Dependent Claim 7 words
The compound of claim 1, methyl 3-(2,3-dimethyl-5-tert-octyl-4-hydroxyphenyl)propionate.
Claim 18
Dependent Claim 7 words
The compound of claim 1, methyl 3-(5,6,7,8-tetrahydro-4-hydroxy-3-tert.-butylnaphthyl-1)propionate.
Claim 19
Dependent Claim 7 words
The compound of claim 1, n-octadecyl 3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate.
Claim 20
Dependent Claim 7 words
The compound of claim 1, 2-(n-octadecylthio)ethyl 3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate.
Claim 21
Dependent Claim 7 words
The compound of claim 1, cyclohexyl 3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate.
Claim 22
Dependent Claim 7 words
The compound of claim 1, 2-ethylhexyl 3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate.
Claim 23
Dependent Claim 7 words
The compound of claim 1, n-octadecyl 3-(5-tert.-octyl-2,3-dimethyl-4-hydroxyphenyl)propionate.
Claim 24
Dependent Claim 7 words
The compound of claim 1, n-octadecyl 3-(5,6,7,8-tetrahydro-4-hydroxy-3-tert.-butyl-naphthyl-1)propionate.
Claim 25
Dependent Claim 7 words
The compound of claim 1, 2,2-dimethylpropylene bis-[3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate].
Claim 26
Dependent Claim 7 words
The compound of claim 1, 1,6-hexamethylene bis-[3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate].
Claim 27
Dependent Claim 7 words
The compound of claim 1, neopentanetetrayl tetrakis-[3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate].
Claim 28
Dependent Claim 7 words
The compound of claim 1, neopentanetetrayl tetrakis-[3-(5-tert.-octyl-2,3-dimethyl-4-hydroxyphenyl)propionate].
Claim 29
Dependent Claim 7 words
The compound of claim 1, methyl 5-tert.-butyl-2,3-dimethyl-4-hydroxyphenylacetate.
Claim 30
Dependent Claim 7 words
The compound of claim 1, n-octadecyl 5-tert.-butyl-2,3-dimethyl-4-hydroxyphenylacetate.
Claim 31
Dependent Claim 7 words
The compound of claim 1, n-butyl 5-tert.-butyl-2,3-dimethyl-4-hydroxyphenylacetate.
Claim 32
Dependent Claim 7 words
The compound of claim 1, n-octyl 5-tert.-butyl-2,3-dimethyl-4-hydroxyphenylacetate.
Claim 33
Dependent Claim 7 words
The compound of claim 1, n-dodecyl 5-tert.-butyl-2,3-dimethyl-4-hydroxyphenylacetate.
Claim 34
Dependent Claim 7 words
The compound of claim 1, 2,2-dimethyl-propylene bis-(5-tert.-butyl-2,3-dimethyl-4-hydroxy-phenylacetate).
Claim 35
Dependent Claim 7 words
The compound of claim 1, 1,6-hexamethylene bis-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenylacetate).
Claim 36
Dependent Claim 7 words
The compound of claim 1, p-tert.-octyl-phenyl 3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate.
Claim 37
Dependent Claim 7 words
The compound of claim 1, phenyl 3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate.
Claim 38
Dependent Claim 7 words
The compound of claim 1, o-tolyl 3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate.
Claim 39
Dependent Claim 6 words
The compound of claim 1, 2,4-di-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate.
Claim 40
Dependent Claim 7 words
The compound of claim 1, neopentanetriyl tris-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenylacetate).
Claim 41
Dependent Claim 7 words
The compound of claim 1, thiodiethylene bis-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenylacetate).
Claim 42
Dependent Claim 7 words
The compound of claim 1, thiodiethylene bis-[3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate].
Claim 43
Dependent Claim 7 words
The compound of claim 1, neopentanetetrayl tetrakis-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenylacetate).
Claim 44
Dependent Claim 7 words
The compound of claim 1, 2,2-dimethyl-1,2,2-pentanetriyl tris-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenylacetate).
Claim 45
Dependent Claim 7 words
The compound of claim 1, 3,6-dioxa-1,8-octamethylene bis-[3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propioate].
Claim 46
Dependent Claim 7 words
The compound of claim 1, ethylene bis-[3-(5-tert.-butyl-2,3-dimethyl-4-hydroxyphenyl)propionate].
Claim 47
Dependent Claim 70 words
A compound according to claim 1 wherein R is tert-butyl, R 1 and R 2 are methyl, R 3 is alkyl of 1 to 18 carbon atoms; 2-(n-octadecylthio)ethyl; alkylene of 2 to 6 carbon atoms; thiodiethylene; 3,6-dioxa-1,8-octamethylene; or a polyvalent saturated aliphatic hydrocarbon radical of 5 to 7 carbon atoms where n is 3 or 4, A is methylene or ethylene, and n is an integer of 1 to 4.

References Cited (Backward Citations)

GB874236A Cited
FR1337163A Cited
US3642868A Cited
US3644482A Cited
FR1436393A Cited
US3285855A Cited
US3646110A Cited
DE1936280A1 Cited
US3654349A Cited
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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) 1979-10-05 1980-04-05 1980-10-05 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-10-05 1984-04-05 1984-10-05 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-10-05 1988-04-05 1988-10-05 $7700.00 Window Closed / Lapsed

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