US4003889A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1,3-Diaryl-2-pyrazoline derivatives
Assignee: Sandoz AG
•
Filing: 1974-06-17
•
Granted: 1977-01-18
•
Expires: 1994-06-17
Abstract
Abstract Disclosed are compounds of formula I, <IMAGE> in which either R1, R2 and R3, which may be the same or different, each signifies a hydrogen atom, a chlorine or fluorine atom, an alkyl radical of 1 to 4 carbon atoms, an alkoxy radical of 1 to 4 carbon atoms, a cyano group, a group -SO3M, an unsubstituted phenyl radical or a phenyl radical substituted by up to 2 substituents selected from chlorine, fluorine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and the group -SO3M, with the proviso that only one of R1, R2 and R3 signifies an unsubstituted or substituted phenyl radical, OR TWO OF R1, R2 and R3 together form a methylenedioxy group, the other of R1, R2 and R3 having one of the above significances, R4 signifies a hydrogen atom, a chlorine or fluorine atom, an alkyl radical of 1 to 4 carbon atoms or an alkoxy radical of 1 to 4 carbon atoms, R5 signifies a hydrogen atom, an alkyl radical of 1 to 4 carbon atoms, an unsubstituted phenyl radical or a phenyl radical substituted by 1 or 2 substituents selected from chlorine, fluorine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and the group -SO3M, A1 signifies a C1 to C3 alkylene chain, unsubstituted or substituted by up to two alkyl groups of 1 to 4 carbon atoms, A2 signifies a C1 to C3 alkylene chain, unsubstituted or substituted by up to two alkyl groups of 1 to 4 carbon atoms; or a phenylene group, unsubstituted or substituted by up to 2 substituents selected from chlorine, fluorine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and the group -SO3M, Y signifies -O- or -NR6-, in which R6 signifies a hydrogen atom or an alkyl radical of 1 to 4 carbon atoms, and THE Ms, which may be the same or different, each signifies a hydrogen atom, or a non-chromophoric cation; THEIR PRODUCTION AND USE AS OPTICAL BRIGHTENING AGENTS PARTICULARLY FOR TEXTILE SUBSTRATES COMPRISING POLYAMIDE FIBERS.
Inventors
- 👤 Ivan Joseph Bolton
- 👤 Alec Victor Mercer
- 👤 Fritz Fleck
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 15:51
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/06
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
369 words
A compound of the formula, ##STR72##in which either R 1 , R 2 and R 3 , which may be the same or different, each signifies a hydrogen atom, a chloro or fluoro radical, an alkyl radical of 1 to 4 carbon atoms, an alkoxy radical of 1 to 4 carbon atoms, a cyano group, a group -- SO 3 M, an unsubstituted phenyl radical or a phenyl radical substituted by up to 2 substituents selected from chloro, fluoro, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and the group --SO 3 M, with the proviso that only one of R 1 , R 2 and R 3 signifies an unsubstituted or substituted phenyl radical, or two of R 1 , r 2 and R 3 together form a methylenedioxy group, the other of R 1 , R 2 and R 3 having one of the above significances, R 4 signifies a hydrogen atom, a chloro or fluoro radical, an alkyl radical of 1 to 4 carbon atoms or an alkoxy radical of 1 to 4 carbon atoms, R 5 signifies a hydrogen atom, an alkyl radical of 1 to 4 carbon atoms, an unsubstituted phenyl radical or a phenyl radical substituted by 1 or 2 substituents selected from chloro, fluoro, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and the group --SO 3 M, A 1 signifies a C 1 to C 3 alkylene chain, unsubstituted or substituted by up to two alkyl groups of 1 to 4 carbon atoms, A 2 signifies a C 1 to C 3 alkylene chain, unsubstituted or substituted by up to two alkyl groups of 1 to 4 carbon atoms; or a phenylene group, unsubstituted or substituted by up to 2 substituents selected from chloro, fluoro, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and the group --SO 3 M, Y signifies --O-- or --NR 6 --, in which R 6 signifies a hydrogen atom or an alkyl radical of 1 to 4 carbon atoms, and the Ms, which may be the same or different, each signifies a hydrogen atom, or a non-chromophoric cation.
Claim 2
Dependent Claim
369 words
A compound of the formula, ##STR72##in which either R 1 , R 2 and R 3 , which may be the same or different, each signifies a hydrogen atom, a chloro or fluoro radical, an alkyl radical of 1 to 4 carbon atoms, an alkoxy radical of 1 to 4 carbon atoms, a cyano group, a group -- SO 3 M, an unsubstituted phenyl radical or a phenyl radical substituted by up to 2 substituents selected from chloro, fluoro, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and the group --SO 3 M, with the proviso that only one of R 1 , R 2 and R 3 signifies an unsubstituted or substituted phenyl radical, or two of R 1 , r 2 and R 3 together form a methylenedioxy group, the other of R 1 , R 2 and R 3 having one of the above significances, R 4 signifies a hydrogen atom, a chloro or fluoro radical, an alkyl radical of 1 to 4 carbon atoms or an alkoxy radical of 1 to 4 carbon atoms, R 5 signifies a hydrogen atom, an alkyl radical of 1 to 4 carbon atoms, an unsubstituted phenyl radical or a phenyl radical substituted by 1 or 2 substituents selected from chloro, fluoro, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and the group --SO 3 M, A 1 signifies a C 1 to C 3 alkylene chain, unsubstituted or substituted by up to two alkyl groups of 1 to 4 carbon atoms, A 2 signifies a C 1 to C 3 alkylene chain, unsubstituted or substituted by up to two alkyl groups of 1 to 4 carbon atoms; or a phenylene group, unsubstituted or substituted by up to 2 substituents selected from chloro, fluoro, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and the group --SO 3 M, Y signifies --O-- or --NR 6 --, in which R 6 signifies a hydrogen atom or an alkyl radical of 1 to 4 carbon atoms, and the Ms, which may be the same or different, each signifies a hydrogen atom, or a non-chromophoric cation.
Claim 3
Dependent Claim
21 words
A compound of claim 1, wherein any phenyl radical as R 1 , R 2 or R 3 , is unsubstituted.
Claim 4
Dependent Claim
10 words
A compound of claim 2, wherein R 4 signifies hydrogen.
Claim 5
Dependent Claim
148 words
A compound of claim 1, of the formula ##STR73##in which R 1 ', R 2 ' and R 3 ', independently, each signifies a hydrogen atom, a chloro or fluoro radical or an alkyl or alkoxy radical of 1 to 4 carbon atoms, R 4 ' signifies a hydrogen atom, a chloro or fluoro radical or an alkyl or alkoxy radical of 1 to 4 carbon atoms, R 5 ' signifies hydrogen, C 1 -4 alkyl, or phenyl, A 1 ' signifies an unsubstituted C 1 -C 3 alkylene chain, A 2 ' signifies an unsubstituted C 1 -C 3 alkylene chain, a further unsubstituted phenylene radical or a phenylene radical further substituted by a --SO 3 M or C 1 -4 alkyl group, and Y' signifies --O-- or ##STR74##in which R 6 ' signifies a hydrogen atom or an alkyl radical of up to 2 carbon atoms.
Claim 6
Dependent Claim
13 words
A compound of claim 4, wherein R 4 ' signifies a hydrogen atom.
Claim 7
Dependent Claim
22 words
A compound of claim 5, wherein, where R 5 ' signifies a C 1 -4 alkyl radical, such is a methyl radical.
Claim 8
Dependent Claim
29 words
A compound of claim 6, wherein the SO 2 A'--CO--Y'--A 2 '--SO 3 M group is in the para position of the phenyl radical to which it is attached.
Claim 9
Dependent Claim
21 words
A compound of claim 4, of the formula ##STR75##in which A 2 " signifies an unsubstituted C 1 -3 alkylene chain.
Claim 10
Dependent Claim
13 words
A compound of claim 8, wherein R 4 ' signifies a hydrogen atom.
Claim 11
Dependent Claim
29 words
A compound of claim 8, wherein the --SO 2 --A'--CO--Y'--A 2 "--SO 3 M group is in the para position of the phenyl radical to which it is attached.
Claim 12
Dependent Claim
75 words
A compound of claim 4, of the formula ##STR76##in which R 2 '" signifies chloro and either R 1 '" and R 3 '" both signify hydrogen, or R 1 '" signifies chloro and R 3 '" signifies methyl, A 1 '" signifies an unsubstituted alkylene radical of up to 2 carbon atoms, Y'" signifies --O--, --NH-- or ##STR77##A 2 '" signifies a further unsubstituted phenylene radical, or an alkylene radical of two carbon atoms.
Claim 13
Dependent Claim
17 words
A compound of claim 11, wherein any phenylene radical as A 2 '" is a 1,4-phenylene radical.
Claim 14
Dependent Claim
17 words
A compound of claim 11, wherein any phenylene radical as A 2 '" is a 1,3-phenylene radical.
Claim 15
Dependent Claim
89 words
A compound of claim 4, of the formula ##STR78##in which R 2 '" signifies chloro, and either R 1 '" and R 3 '" both signify hydrogen, or R 1 '" signifies chloro and R 3 '" signifies methyl, A 1 iv signifies an unsubstituted alkylene radical of up to 2 carbon atoms, A 2 iv signifies an ethylene group, a further unsubstituted phenylene radical or a phenylene radical substituted by a --SO 3 M or C 1 -4 alkyl group, and Y iv signifies --O--, --NH-- or ##STR79##
Claim 16
Dependent Claim
17 words
A compound of claim 14, wherein A 1 IV signifies an alkylene radical of 2 carbon atoms.
Claim 17
Dependent Claim
32 words
A compound of claim 14, wherein, where A 2 IV signifies a phenylene radical substituted by a C 1 -4 alkyl radical, such is a phenylene radical substituted by a methyl radical.
Claim 18
Dependent Claim
14 words
A compound of claim 16, wherein Y IV signifies --NH-- or --N(CH 3 )-.
Claim 19
Dependent Claim
77 words
A compound of claim 8, of the formula in which R 1 ", r 2 " and R 3 ", which may be the same or different, each signifies a hydrogen atom, a chloro radical or an alkyl radical of up to 2 carbon atoms, Y" signifies --O----NH-- or ##STR80##A 1 " signifies an unsubstituted alkylene radical of up to 2 carbon atoms, A 2 v signifies an unsubstituted alkylene radical of 2 or 3 carbon atoms.
Claim 20
Dependent Claim
8 words
A compound of claim 17, of formula ##STR81##20.
Claim 21
Dependent Claim
7 words
A compound of claim 17, of formula
Claim 22
Dependent Claim
7 words
A compound of claim 17, of formula
Claim 23
Dependent Claim
7 words
A compound of claim 17, of formula
Claim 24
Dependent Claim
7 words
A compound of claim 17, of formula
Claim 25
Dependent Claim
7 words
A compound of claim 17, of formula
Claim 26
Dependent Claim
7 words
A compound of claim 17, of formula
Claim 27
Dependent Claim
79 words
A compound of claim 1, in which M signifies a hydrogen atom, an alkali metal cation or a cation R 7 R 8 R 9 R 10 N + , in which R 7 , R 8 , R 9 and R 10 , independently, each signifies a hydrogen atom or an alkyl radical of 1 to 4 carbon atoms, unsubstituted or substituted by up to two substituents selected from alkyl of up to 2 carbon atoms and hydroxy.
Claim 28
Dependent Claim
26 words
A compound of claim 26, wherein, where M signifies a cation R 7 R 8 R 9 R 10 N + , R 10 signifies hydrogen.
Claim 29
Dependent Claim
16 words
A compound of claim 27, wherein R 7 , R 8 and R 9 signify hydrogen.
Claim 30
Dependent Claim
13 words
A compound of claim 26, wherein M signifies hydrogen or a sodium cation.
Claim 31
Dependent Claim
11 words
A compound of claim 29, wherein M signifies a sodium cation.
References Cited (Backward Citations)
US3378389A
Cited
US3560485A
Cited
GB1204953A
Cited
US3522242A
Cited
US3629241A
Cited
US3690947A
Cited
US3849406A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-01-18 | 1980-07-19 | 1981-01-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-18 | 1984-07-19 | 1985-01-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-18 | 1988-07-19 | 1989-01-18 | $7700.00 | Window Closed / Lapsed |