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US4759862A
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O,p-bifunctionalized o'-substituted phenols
Assignee: BASF Corp
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Filing: 1987-07-30
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Granted: 1988-07-26
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Expires: 2007-07-30
Abstract
Abstract Novel bifunctionalized o-substituted phenols of the formula I ##STR1## are described. Reference should be made to the description in respect of the meaning of the substituents R 1 , Y and Z. The novel substances are suitable as stabilizers for organic polymers and for mineral oils or synthetic oils.
Inventors
- 👤 Hans R. Meier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 19:58
CPC Classifications
C; C10; C10M; C10M135/00; C10M135/32; C10M135/36; C07; C07C; C07C323/00; C08; C08K; C08K5/00; C08K5/36; C08K5/37; C08K5/375; C09; C09K; C09K15/00; C09K15/04; C09K15/06; C09K15/08; C10M135/20; C10M2219/00; C10M2219/08; C10M2219/082; C10M2219/084; C10M2219/085; C10M2219/087; C10M2219/089; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
488 words
A compound of the formula I ##STR20## in which R 1 is C 2 -C 20 -alkyl, C 3 -C 20 -alkenylmethyl, C 3 -C 20 -alkinylmethyl, C 5 -C 12 -cycloalkyl, phenyl, 1- or 2-naphthyl, C 7 -C 14 -alkaryl or C 7 -C 14 -aralkyl, Y is --CH 2 --S--R 2 and Z is --CH 2 --S--R 3 , or in which Y and/or Z is a radical ##STR21## in which R 2 , R 3 , R 4 and R 5 independently of one another are C 1 -C 20 -alkyl, C 2 -C 20 -alkyl which is substituted by a phenyl radical and/or one or two hydroxyl groups, C 3 -C 20 -alkenylmethyl, C 3 -C 20 -alkinylmethyl, C 5 -C 12 -cycloalkyl, phenyl, 1- or 2-naphthyl, C 7 -C 14 -alkaryl, C 7 -C 14 -aralkyl, C 5 -C 7 -cycloalkyl which is substituted by hydroxyl in the 2-position or radicals of the formulae --C(R 6 R 7 )--(CHR 8 ) m --W, --(CH 2 ) 2 --OCO--R 15 or ##STR22## in which m is 0, 1 or 2, R 6 , R 7 and R 8 independently of one another are hydrogen or C 1 -C 6 -alkyl, W is a radical --COR 9 , --CN, --COOR 10 or --CON(R 10 R 11 ), in which R 9 is hydrogen, C 1 -C 20 -alkyl, phenyl, 1- or 2-naphthyl, C 5 -C 12 -cycloalkyl, C 7 -C 14 -aralkyl or C 7 -C 14 -alkaryl and in which R 10 and R 11 independently of one another have the meanings of R 9 , or are additionally C 2 -C 20 -alkyl which is substituted by a hydroxyl or cyano group, or are C 3 -C 20 -alkyl which is interrupted by one to five --O--, --S--, --N(CH 3 )-- or --N(C 2 H 5 )-- and is unsubstituted or substituted by a hydroxyl group, it being necessary for the several heteroatoms which may occur to be separated by at least one methylene group, in which R 10 or R 11 is C 2 -C 12 -alkenyl, C 2 -C 12 -alkinyl, phenyl which is substituted by one or two --NO 2 , --Cl, --Br, --OCH 3 or --COOR 18 , or a group ##STR23## in which R 12 , R 13 and R 14 independently of one another are hydrogen, C 1 -C 20 -alkyl, cyclohexyl or phenyl, in which R 15 is C 1 -C 20 -alkyl, C 5 -C 12 -cycloalkyl, C 7 -C 14 -aralkyl, C 7 -C 14 -alkaryl, phenyl, 1- or 2-naphthyl or a radical ##STR24## in which X is --C(R 16 R 17 )--, --S-- or --S--S--, in which R 16 and R 17 independently of one another are hydrogen, C 1 -C 6 -alkyl, cyclohexyl or phenyl, and in which, finally, R 18 is C 1 -C 6 -alkyl, cyclohexyl, phenyl, benzyl or tolyl.
Claim 2
Dependent Claim
488 words
A compound of the formula I ##STR20## in which R 1 is C 2 -C 20 -alkyl, C 3 -C 20 -alkenylmethyl, C 3 -C 20 -alkinylmethyl, C 5 -C 12 -cycloalkyl, phenyl, 1- or 2-naphthyl, C 7 -C 14 -alkaryl or C 7 -C 14 -aralkyl, Y is --CH 2 --S--R 2 and Z is --CH 2 --S--R 3 , or in which Y and/or Z is a radical ##STR21## in which R 2 , R 3 , R 4 and R 5 independently of one another are C 1 -C 20 -alkyl, C 2 -C 20 -alkyl which is substituted by a phenyl radical and/or one or two hydroxyl groups, C 3 -C 20 -alkenylmethyl, C 3 -C 20 -alkinylmethyl, C 5 -C 12 -cycloalkyl, phenyl, 1- or 2-naphthyl, C 7 -C 14 -alkaryl, C 7 -C 14 -aralkyl, C 5 -C 7 -cycloalkyl which is substituted by hydroxyl in the 2-position or radicals of the formulae --C(R 6 R 7 )--(CHR 8 ) m --W, --(CH 2 ) 2 --OCO--R 15 or ##STR22## in which m is 0, 1 or 2, R 6 , R 7 and R 8 independently of one another are hydrogen or C 1 -C 6 -alkyl, W is a radical --COR 9 , --CN, --COOR 10 or --CON(R 10 R 11 ), in which R 9 is hydrogen, C 1 -C 20 -alkyl, phenyl, 1- or 2-naphthyl, C 5 -C 12 -cycloalkyl, C 7 -C 14 -aralkyl or C 7 -C 14 -alkaryl and in which R 10 and R 11 independently of one another have the meanings of R 9 , or are additionally C 2 -C 20 -alkyl which is substituted by a hydroxyl or cyano group, or are C 3 -C 20 -alkyl which is interrupted by one to five --O--, --S--, --N(CH 3 )-- or --N(C 2 H 5 )-- and is unsubstituted or substituted by a hydroxyl group, it being necessary for the several heteroatoms which may occur to be separated by at least one methylene group, in which R 10 or R 11 is C 2 -C 12 -alkenyl, C 2 -C 12 -alkinyl, phenyl which is substituted by one or two --NO 2 , --Cl, --Br, --OCH 3 or --COOR 18 , or a group ##STR23## in which R 12 , R 13 and R 14 independently of one another are hydrogen, C 1 -C 20 -alkyl, cyclohexyl or phenyl, in which R 15 is C 1 -C 20 -alkyl, C 5 -C 12 -cycloalkyl, C 7 -C 14 -aralkyl, C 7 -C 14 -alkaryl, phenyl, 1- or 2-naphthyl or a radical ##STR24## in which X is --C(R 16 R 17 )--, --S-- or --S--S--, in which R 16 and R 17 independently of one another are hydrogen, C 1 -C 6 -alkyl, cyclohexyl or phenyl, and in which, finally, R 18 is C 1 -C 6 -alkyl, cyclohexyl, phenyl, benzyl or tolyl.
Claim 3
Dependent Claim
21 words
A compound of the formula I according to claim 1, in which R 1 is branched C 3 -C 12 -alkyl.
Claim 4
Dependent Claim
16 words
A compound of the formula I according to claim 1, in which R 1 is tert.-butyl.
Claim 5
Dependent Claim
26 words
A compound of the formula I according to claim 1, in which Y is --CH 2 --S--R 2 and Z is --CH 2 S--R 3 .
Claim 6
Dependent Claim
288 words
A compound of the formula I according to claim 1, in which R 1 is branched C 3 -C 12 -alkyl, C 5 -C 9 -cycloalkyl, phenyl or C 7 -C 9 -aralkyl, in which R 2 and R 3 independently of one another are C 4 -C 14 -alkyl, C 2 -C 14 -alkyl which is substituted by a phenyl and/or one or two hydroxyl groups, allyl, propargyl, C 5 -C 9 -cycloalkyl, 2-hydroxycyclohexyl, phenyl, or C 7 -C 9 -aralkyl, or are a radical --C(R 6 R 7 )--(CHR 8 ) m --W, --(CH 2 ) 2 --OCO--R 15 or ##STR25## in which m is 0, 1 or 2, and in which R 6 , R 7 and R 8 independently of one another are hydrogen or methyl, W is --COOR 10 or --CON(R 10 R 11 ), in which R 10 and R 11 independently of one another are hydrogen, C 1 -C 12 -alkyl, phenyl, C 5 -C 9 -cycloalkyl, C 7 -C 9 -aralkyl, 2-hydroxyethyl, 2-cyanoethyl, or C 3 -C 12 -alkyl which is interrupted by one to three --O-- and is unsubstituted or substituted by a hydroxyl group, it being necessary for several oxygen atoms which may occur to be separated by at least one methylene group, in which R 10 and R 11 are allyl, propargyl, phenyl which is substituted by a --Cl, --COOCH 3 or --OCH 3 , or a radical ##STR26## in which R 12 , R 13 and R 14 independently of one another are hydrogen or C 1 -C 12 -alkyl, and in which R 15 is C 1 -C 12 -alkyl, C 5 -C 9 -cycloalkyl, C 7 -C 9 -aralkyl, phenyl or a radical ##STR27##
Claim 7
Dependent Claim
45 words
A compound of the formula I according to claim 1, in which R 1 is tert.-butyl, cyclohexyl, phenyl or benzyl, and in which R 2 and R 3 independently of one another are C 4 -C 14 -alkyl, 2-hydroxyethyl, 2,3-dihydroxypropyl, 1-phenyl-2-hydroxyethyl, cyclohexyl, phenyl or benzyl.
Claim 8
Dependent Claim
81 words
A compound of the formula I according to claim 1, in which R 1 is tert.-butyl, cyclohexyl, phenyl or benzyl, in which R 2 and R 3 are radicals of the formula --(CH 2 ) m+1 --W, in which W is --COOR 10 or --CON(R 10 R 11 ), and in which R 10 and R 11 independently of one another denote hydrogen, C 1 -C 12 -alkyl, phenyl, cyclohexyl, benzyl, 2-hydroxyethyl, 2-hydroxypropyl, 5-hydroxy-3-oxapentyl or 3-oxabutyl, or are a radical ##STR28##
Claim 9
Dependent Claim
30 words
A compound of the formula I according to claim 1, in which R 1 is tert.-butyl and R 2 and R 3 are each 2-ethyl-hexyl, t-octyl, n-dodecyl or t-dodecyl radicals.
Claim 10
Dependent Claim
19 words
The compound of the formula I according to claim 8, in which R 2 and R 3 are n-octyl.
Claim 11
Dependent Claim
19 words
The compound of the formula I according to claim 8, in which R 2 and R 3 are n-dodecyl.
Claim 12
Dependent Claim
18 words
The compound of formula I according to claim 1 in which R 2 and R 2 are 2-ethylhexyl.
Claim 13
Dependent Claim
34 words
A stabilized composition which comprises (a) a polymer, a mineral oil lubricant or a synthetic lubricant, and (b) an effective stabilizing amount of at least one compound of formula I according to claim 1.
Claim 14
Dependent Claim
32 words
A stabilized composition which comprises (a) an elastomer, a mineral oil lubricant or a synthetic lubricant, and (b) an effective stabilizing amount of a compound of formula I according to claim 6.
Claim 15
Dependent Claim
72 words
A compound of formula I ##STR29## in which R 1 is C 2 -C 20 -alkyl, C 3 -C 20 -alkenylmethyl, C 3 -C 20 -alkynylmethyl, C 5 -C 12 -cycloalkyl, phenyl, 1-naphthyl, 2-naphthyl, C 7 -C 14 -alkaryl or C 7 -C 14 -aralkyl, Y is --CH 2 --S--R 2 and Z is --CH 2 --S--R 3 , where R 2 and R 3 are independently C 1 -C 20 -alkyl.
Claim 16
Dependent Claim
72 words
A compound of formula I ##STR29## in which R 1 is C 2 -C 20 -alkyl, C 3 -C 20 -alkenylmethyl, C 3 -C 20 -alkynylmethyl, C 5 -C 12 -cycloalkyl, phenyl, 1-naphthyl, 2-naphthyl, C 7 -C 14 -alkaryl or C 7 -C 14 -aralkyl, Y is --CH 2 --S--R 2 and Z is --CH 2 --S--R 3 , where R 2 and R 3 are independently C 1 -C 20 -alkyl.
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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) | 1991-07-26 | 1992-01-25 | 1992-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-07-26 | 1996-01-25 | 1996-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-07-26 | 2000-01-25 | 2000-07-26 | $7700.00 | Window Closed / Lapsed |