US4484000A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Hydroquinones
Assignee: BASF Schweiz AG
•
Filing: 1982-06-18
•
Granted: 1984-11-20
•
Expires: 2002-06-18
Abstract
Abstract New hydroquinones having the formula: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2; R is a residue of formula: ##STR2## wherein Q is selected from the residues --COZR 4 wherein Z is 0 or NR 5 , --OX wherein X is R 5 or --COR 7 , --NR 8 R 9 , --PO(OR 10 )[O] x R 11 wherein x is 0 or 1, --SO 2 R 12 or --CN, and salts thereof with organic or inorganic acid bases. The groups, R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , k and n are defined hereafter. These compounds are used as stabilizers in photographic materials.
Inventors
- 👤 Frederick H. Howell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 16:50
CPC Classifications
G; G03; G03C; G03C7/00; G03C7/30; G03C7/392; G03C7/39208; G03C7/39212; G03C7/39216; C; C07; C07C; C07C37/00; C07C37/11; C07C37/14; C07C39/00; C07C39/02; C07C39/11; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/178; C07C43/1782; C07C43/1783; C07C67/00; C07C67/28; C07C67/293; C07C67/30; C07C67/333; C07C67/343; C07C67/347; C07D; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/40; C07F9/4003; C07F9/4006; C07F9/4056; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
471 words
Hydroquinone compounds having the formula: ##STR14## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2; R is a residue of formula: ##STR15## wherein Q is selected from the residues: --COZR 4 wherein Z is O or NR 5 , and R 4 independently is H, a straight or branched chain alkyl having from 1 to 20 carbon atoms, optionally interrupted by 1 to five oxygen atoms, and optionally substituted by a group OR 6 wherein R 6 is C 1 -C 12 alkyl, C 3 -C 12 cycloalkyl, straight or branch C 3 -C 20 alkenyl, C 6 -C 10 aryl or C 7 -C 13 aralkyl, or R 4 is a straight or branched chain alkenyl group having from 3 to 20 carbon atoms, a cycloalkyl group having from 3 to 12 carbon atoms, an aryl group having from 6 to 10 carbon atoms optionally substituted by a C 1 -C 4 alkyl group; or an aralkyl group having from 7 to 13 carbon atoms, a 5- or 6-membered heterocycle containing an oxygen atom and optionally substituted by one or two C 1 -C 4 straight- or branch chain alkyl groups; or methyl substituted by a 5- or 6-membered heterocycle containing an oxygen atom and optionally substituted by one or two C 1 -C 4 straight- or branch chain alkyl groups; and when Z is --NR 5 , R 5 is hydrogen or a straight or branched chain alkyl group having from 1 to 20 carbon atoms, or R 4 and R 5 together with the nitrogen atom to which they are each bonded may form a 5- or 6-membered heterocyclic ring, optionally substituted by one or two C 1 -C 4 alkyl groups; n is an integer from 1 to 20; k is 1 or 2; 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 and 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 have their previous significance, R 1 is C 1 -C 8 straight or branched chain alkyl, or a residue of formula II as hereinbefore defined, and when R 1 is a residue of formula II, then R 1 and R may be the same or different; and salts thereof with organic or inorganic acids and bases.
Claim 2
Dependent Claim
471 words
Hydroquinone compounds having the formula: ##STR14## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2; R is a residue of formula: ##STR15## wherein Q is selected from the residues: --COZR 4 wherein Z is O or NR 5 , and R 4 independently is H, a straight or branched chain alkyl having from 1 to 20 carbon atoms, optionally interrupted by 1 to five oxygen atoms, and optionally substituted by a group OR 6 wherein R 6 is C 1 -C 12 alkyl, C 3 -C 12 cycloalkyl, straight or branch C 3 -C 20 alkenyl, C 6 -C 10 aryl or C 7 -C 13 aralkyl, or R 4 is a straight or branched chain alkenyl group having from 3 to 20 carbon atoms, a cycloalkyl group having from 3 to 12 carbon atoms, an aryl group having from 6 to 10 carbon atoms optionally substituted by a C 1 -C 4 alkyl group; or an aralkyl group having from 7 to 13 carbon atoms, a 5- or 6-membered heterocycle containing an oxygen atom and optionally substituted by one or two C 1 -C 4 straight- or branch chain alkyl groups; or methyl substituted by a 5- or 6-membered heterocycle containing an oxygen atom and optionally substituted by one or two C 1 -C 4 straight- or branch chain alkyl groups; and when Z is --NR 5 , R 5 is hydrogen or a straight or branched chain alkyl group having from 1 to 20 carbon atoms, or R 4 and R 5 together with the nitrogen atom to which they are each bonded may form a 5- or 6-membered heterocyclic ring, optionally substituted by one or two C 1 -C 4 alkyl groups; n is an integer from 1 to 20; k is 1 or 2; 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 and 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 have their previous significance, R 1 is C 1 -C 8 straight or branched chain alkyl, or a residue of formula II as hereinbefore defined, and when R 1 is a residue of formula II, then R 1 and R may be the same or different; and salts thereof with organic or inorganic acids and bases.
Claim 3
Dependent Claim
61 words
Compounds according to claim 1 wherein p, q, R, Q, R 1 , R 2 , R 3 , R 4 , R 5 , n and k are as defined in claim 1, R 6 is C 3 -C 12 cycloalkyl, straight or branch C 3 -C 20 alkenyl, C 6 -C 10 aryl or C 7 -C 13 aralkyl.
Claim 4
Dependent Claim
20 words
Compounds according to claim 1 wherein the groups R and R 1 are bonded in the 2- or 5-positions, respectively.
Claim 5
Dependent Claim
54 words
Compounds according to claim 1 having the formula III: ##STR16## wherein R 2 , R 3 , n, k and Q are as defined in claim 1 and R 1 is a group of formula II, as defined in claim 1, or is a group of formula IV: ##STR17## as well as salts thereof.
Claim 6
Dependent Claim
88 words
Compounds of formula III according to claim 4 wherein Q is --COZR 4 , R 2 and R 3 , independently, are methyl, ethyl, n-propyl, isopropyl or neopentyl, or either R 2 or R 3 is optionally substituted by a group --COOR 4 , or R 2 or R 3 may be so linked to the residue C n H 2n+1-k that there is formed a cycloalkylene residue having 5 to 8 carbon atoms which is substituted by --COOR 4 , as well as salts of these compounds.
Claim 7
Dependent Claim
206 words
Compounds of formula III according to claim 5 wherein k is 1, R 1 is residue II or IV, Q is --COZR 4 , n is an integer from 1 to 10, R 2 and R 3 , independently, are methyl, ethyl or neopentyl, or one of R 2 and R 3 may be so linked to the residue --C n H 2n+1-k that there is formed a cyclohexylene residue which is substituted by --COOR 4 , R 4 is hydrogen, C 1-20 alkyl (optionally interrupted by 1, 2 or 3 oxygen atoms and/or optionally substituted by --OR 6 wherein R 6 is cyclopentyl, cyclohexyl, cyclooctyl, C 3-10 alkenyl, phenyl, benzyl, phenethyl, benzhydryl or naphthylmethyl) or R 4 is C 3 -C 15 alkenyl, phenyl optionally substituted by 1 or 2 C 1-4 alkyl groups, benzyl, phenethyl, cyclopentyl, cyclohexyl or a 5- or 6-membered heterocyclic ring containing an oxygen atom, which ring is optionally substituted by 1 or 2 C 1-4 alkyl groups, or R 4 and R 5 , together with the nitrogen atom to which they are each bonded, may form a 5- or 6-membered heterocyclic ring, optionally substituted by one or two C 1-4 alkyl groups; as well as salts of these compounds.
Claim 8
Dependent Claim
170 words
Compounds of formula III according to claim 6 wherein k is 1, Q is --COZR 4 , n is an integer from 1 to 10, R 2 and R 3 , independently, are methyl, ethyl or neopentyl, or one of R 2 and R 3 may be so linked to the residue --C n H 2n+1-k that there is formed a cyclohexylene residue which is substituted by --COOR 4 , R 4 is hydrogen, C 1-20 alkyl (optionally interrupted by 1 or 2 oxygen atoms and/or optionally substituted by cyclohexyloxy, C 3-10 -alkenyloxy, phenoxy or benzyloxy) or R 4 is C 3-15 -alkenyl, phenyl, benzyl, phenethyl, cyclopentyl, cyclohexyl, a 5- or 6-membered heterocyclic ring containing an oxygen atom, and R 5 is hydrogen or C 1-15 alkyl, or R 4 and R 5 , together with the nitrogen atom to which they are each bonded, may form a 5- or 6-membered heterocyclic ring optionally substituted by one or two C 1-4 alkyl groups; as well as salts of these compounds.
Claim 9
Dependent Claim
84 words
Compounds of formula III according to claim 7, wherein R 4 is C 1-16 alkyl (optionally substituted by an oxygen atom or optionally substituted by phenoxy) or R 4 is C 3-15 -alkenyl, phenyl, benzyl, tetrahydrofuran-3-yl, tetrahydrofuran-4-yl or tetrahydrofurfuryl, or R 4 and R 5 , together with the nitrogen atom to which they are each bonded, may form a 5- or 6-membered heterocyclic ring optionally substituted by one or two C 1 -C 4 alkyl groups; as well as salts of these compounds.
Claim 10
Dependent Claim
108 words
Compounds of formula III according to claim 8 wherein, Q is --COZR 4 n is an integer from 1 to 3, R 2 and R 3 are each methyl or neopentyl, R 4 is hydrogen, C 1-16 alkyl (optionally substituted by an oxygen atom or optionally substituted by phenoxy) or R 4 is phenyl, benzyl or tetrahydrofuran-3-yl, R 5 is hydrogen or C 1-15 alkyl, or R 4 and R 5 , together with the nitrogen atom to which they are each bonded, may form a 5- or 6-membered heterocyclic ring optionally substituted by 1 or 2 C 1-4 alkyl groups; as well as salts of these compounds.
Claim 11
Dependent Claim
8 words
A compound of claim 1 which is 2',5'-bis-(5-methoxycarbonyl-2-methylpent-2-yl)-hydroquinone.
Claim 12
Dependent Claim
11 words
A compound of claim 1 which is 2',5'-bis-(5-carboxy-2-methyl-pent-2-yl) hydroquinone, di(n-hexyl) ester.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-11-20 | 1988-05-21 | 1988-11-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-11-20 | 1992-05-21 | 1992-11-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-11-20 | 1996-05-21 | 1996-11-20 | $7700.00 | Window Closed / Lapsed |