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US4904815A Expired / Lapsed US ⏱️ 0.0 years remaining

Phenols and their production

Assignee: HA WHITTEN & Co
•
Filing: 1987-10-13
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Granted: 1990-02-27
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Expires: 2007-10-13
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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.

References Cited (Backward Citations)

US3678095A Cited
US3984460A Cited
US3988363A Cited
US4049713A Cited
GB1548595A Cited
US3989738A Cited
GB2083023A Cited
US4390723A Cited
JPH07135049A Cited

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

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