US4904815A
Expired / Lapsed
US
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Phenols and their production
Assignee: HA WHITTEN & Co
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Filing: 1987-10-13
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Granted: 1990-02-27
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Expires: 2007-10-13
Abstract
Abstract New phenols are described containing an alkyl substituent containing a functional group; as well as a process for the production of such phenols. The new phenols are useful e.g. as stabilizers in organic or aqueous systems.
Inventors
- 👤 Frederick H. Howell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 20:00
CPC Classifications
C; C07; C07C; C07C233/00; C07C233/01; C07C233/16; C07C233/17; C07C233/18; C07C205/00; C07C205/13; C07C205/17; C07C215/00; C07C215/46; C07C215/48; C07C215/54; C07C235/00; C07C235/02; C07C235/32; C07C235/38; C07C255/00; C07C255/01; C07C255/32; C07C255/36; C07C255/41; C07C255/45; C07C255/46; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/178; C07C43/1782; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/69; C07C49/00; C07C49/20; C07C49/24; C07C49/245; C07C49/527; C07C49/573; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/3804; C07F9/3882; C07F9/40; C07F9/4003; C07F9/4015; C07F9/4056; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
579 words
A compound having the formula ##STR137## wherein p is 1, 2 or 3; and q is 0, 1 or 2 provided that p+q≦3; R is a group of the formula ##STR138## and when p is 2 or 3, each group R may be the same or different and is present in the 2-, 4- or 6-position; n is an integer from 2 to 30; K is 1 or 2; Q is --COOR 4 or --CONR 4 R 5 wherein R 4 is (1) H; (2) a straight or branched chain alkyl having from 1 to 20 carbon atoms; (3) divalent straight or branched chain alkylene having 2-20 carbon atoms; (4) a straight or branched chain alkenyl group having from 3 to 20 carbon atoms, (5) a cycloalkyl group having from 3 to 12 carbon atoms; (6) an aryl group having from 6 to 10 carbon atoms which is unsubstituted or is substituted by a C 1 -C 4 alkyl group; (7) an aralkyl group having from 7 to 13 carbon atoms; provided that when k is 2, the two carbon atoms to which the --COOR 4 groups are attached are not adjacent to one another; and R 5 is hydrogen or a straight or branched chain alkyl group having from 1 to 20 carbon atoms, or R.sup. 4 or R 5 together with the nitrogen atom to which they are each bonded may form a pyrrolidine, piperidine, morpholine or 2,5-dimethyl morpholine; R 2 and R 3 are the same or different and each is straight or branched chain alkyl group having from 1 to 5 carbon atoms and, when Q is CO 2 R 4 , either R 2 or R 3 is optionally substituted by a --CO 2 R 4 group, the R 4 groups being independent, or R 2 or R 3 may be so linked to the residue C n H 2n+1-k that there is formed a C 5 -C 12 cycloalkylene residue substituted by the group --(CO 2 R 4 ) k , the R 4 groups being independent, wherein R 4 and k are as previously defined; R 1 is a C 1 -C 12 straight or branched chain alkyl group, a C 7 -C 9 aralkyl group, halogen, CF 3 , SH, SR 13 , CO 2 H, CO 2 R.sup. 13, COR 13 , COC 6 H 5 , CONH 2 , CN, SO 3 H, SO 2 NH 2 , PO(OH) 2 , PO(OR 13 ) 2 , or NO 2 wherein R 13 is a C 1 -C 4 straight or branched chain alkyl group, and, when O is 2, each R 1 group may be the same or different; and provided that, when p is 1, R 1 is C 1 -C 12 alkyl, R 2 and R 3 are C 1 -C 5 alkyl, k is 1, O is --COOR 4 wherein R 4 is H, and q is as previously defined, then n is not 2; and further provided that when k is 2 and p is 1 and the group R is in the para-position to the phenolic OH, then in such case (a) when O is --COOR 4 , R 4 is other than straight or branched chain alkyl and unsubstituted or substituted phenyl, and (b) when O is --CONR 4 R 5 , R 4 and R 5 are not both H; or a salt thereof with an organic or inorganic acid or base.
Claim 2
Dependent Claim
579 words
A compound having the formula ##STR137## wherein p is 1, 2 or 3; and q is 0, 1 or 2 provided that p+q≦3; R is a group of the formula ##STR138## and when p is 2 or 3, each group R may be the same or different and is present in the 2-, 4- or 6-position; n is an integer from 2 to 30; K is 1 or 2; Q is --COOR 4 or --CONR 4 R 5 wherein R 4 is (1) H; (2) a straight or branched chain alkyl having from 1 to 20 carbon atoms; (3) divalent straight or branched chain alkylene having 2-20 carbon atoms; (4) a straight or branched chain alkenyl group having from 3 to 20 carbon atoms, (5) a cycloalkyl group having from 3 to 12 carbon atoms; (6) an aryl group having from 6 to 10 carbon atoms which is unsubstituted or is substituted by a C 1 -C 4 alkyl group; (7) an aralkyl group having from 7 to 13 carbon atoms; provided that when k is 2, the two carbon atoms to which the --COOR 4 groups are attached are not adjacent to one another; and R 5 is hydrogen or a straight or branched chain alkyl group having from 1 to 20 carbon atoms, or R.sup. 4 or R 5 together with the nitrogen atom to which they are each bonded may form a pyrrolidine, piperidine, morpholine or 2,5-dimethyl morpholine; R 2 and R 3 are the same or different and each is straight or branched chain alkyl group having from 1 to 5 carbon atoms and, when Q is CO 2 R 4 , either R 2 or R 3 is optionally substituted by a --CO 2 R 4 group, the R 4 groups being independent, or R 2 or R 3 may be so linked to the residue C n H 2n+1-k that there is formed a C 5 -C 12 cycloalkylene residue substituted by the group --(CO 2 R 4 ) k , the R 4 groups being independent, wherein R 4 and k are as previously defined; R 1 is a C 1 -C 12 straight or branched chain alkyl group, a C 7 -C 9 aralkyl group, halogen, CF 3 , SH, SR 13 , CO 2 H, CO 2 R.sup. 13, COR 13 , COC 6 H 5 , CONH 2 , CN, SO 3 H, SO 2 NH 2 , PO(OH) 2 , PO(OR 13 ) 2 , or NO 2 wherein R 13 is a C 1 -C 4 straight or branched chain alkyl group, and, when O is 2, each R 1 group may be the same or different; and provided that, when p is 1, R 1 is C 1 -C 12 alkyl, R 2 and R 3 are C 1 -C 5 alkyl, k is 1, O is --COOR 4 wherein R 4 is H, and q is as previously defined, then n is not 2; and further provided that when k is 2 and p is 1 and the group R is in the para-position to the phenolic OH, then in such case (a) when O is --COOR 4 , R 4 is other than straight or branched chain alkyl and unsubstituted or substituted phenyl, and (b) when O is --CONR 4 R 5 , R 4 and R 5 are not both H; or a salt thereof with an organic or inorganic acid or base.
Claim 3
Dependent Claim
56 words
A compound according to claim 1 and having the formula ##STR139## wherein R 1 , p and q are as defined in claim 1 and R o is a residue of formula: ##STR140## in which R 2 , R 3 , R 4 , R 5 , n and k are as defined in claim 1.
Claim 4
Dependent Claim
10 words
A compound according to claim 2 wherein k is 1.
Claim 5
Dependent Claim
16 words
A compound according to claim 3 wherein R 0 is a residue of the formula: ##STR141##
Claim 6
Dependent Claim
29 words
A compound according to claim 4 wherein R 2 and R 3 are each CH 3 and R 1 is straight or branched chain C 1 -C 5 alkyl.
Claim 7
Dependent Claim
10 words
A compound according to claim 2 wherein n is 3.
Claim 8
Dependent Claim
10 words
A compound according to claim 1 wherein p is 1.
Claim 9
Dependent Claim
10 words
A compound according to claim 7 wherein k is 1.
Claim 10
Dependent Claim
28 words
A compound according to claim 8 wherein R 2 and R 3 are each methyl and R 1 is C 1 -C 5 straight or branched chain alkyl.
Claim 11
Dependent Claim
16 words
A compound according to claim 1 wherein n is an integer of from 3 to 10.
Claim 12
Dependent Claim
17 words
A compound according to claim 2 which does not contain a residue of formula III or IV.
Claim 13
Dependent Claim
10 words
A compound according to claim 1 said compound being 2,4-bis(5-methoxycarbonyl-2-methyl-pent-2-yl)phenol.
Claim 14
Dependent Claim
19 words
A composition comprising a substrate and, as stabiliser, a compound or a salt thereof as defined in claim 1.
Claim 15
Dependent Claim
17 words
A composition according to claim 13 wherein the substrate is an aqueous medium in contact with metals.
Claim 16
Dependent Claim
12 words
A composition according to claim 14 wherein the metals are ferrous metals.
Claim 17
Dependent Claim
17 words
A composition according to claim 13 wherein the substrate is an organic material susceptible to oxidative decomposition.
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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) | 1993-02-26 | 1993-08-28 | 1994-02-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-02-26 | 1997-08-28 | 1998-02-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-02-26 | 2001-08-28 | 2002-02-27 | $7700.00 | Window Closed / Lapsed |