US3984399A
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Bis-stilbene compounds
Assignee: Novartis AG
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Filing: 1974-09-27
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Granted: 1976-10-05
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Expires: 1994-09-27
Abstract
Abstract The present invention provides the new bis-stilbene compounds, which are useful as optical brighteners and correspond to the formula R.sub.1 -- CH = CH -- X -- CH = CH -- R.sub.2 in which X represents a diphenyl residue bound in positions 4 and 4' to the =CH-- groups; R 1 and R 2 independently of each other, each represents a monocyclic benzene residue, a diphenyl, naphthyl or pyridyl residue, and in which at least one of the cyclic systems R 1 , R 2 , X contains a possibly functionally modified sulphonic acid group, a sulphone group, a possibly functionally modified carboxylic acid group, a nitrile, hydroxyl, mercapto or methyl group.
Inventors
- 👤 Kurt Weber
- 👤 Peter Liechti
- 👤 Hans Rudolf Meyer
- 👤 Adolf Emil Siegrist
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 19:36
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/16; C07D295/18; C07D295/182; C07D295/192; C07C; C07C1/00; C07C1/32; C07C1/321; C07C1/324; C07C17/00; C07C17/26; C07C17/263; C07C17/2635; C07C17/32; C07C25/00; C07C25/24; C07C309/00; C07C309/01; C07C309/28; C07C309/29; C07C309/39; C07C309/63; C07C309/72; C07C309/73; C07C309/78; C07C309/86; C07C309/87; C07C311/00; C07C311/15; C07C311/16; C07C311/17; C07C313/00; C07C313/02; C07C313/04; C07C317/00; C07C317/14; C07C45/00; C07C45/44; C07C47/00; C07C47/52; C07C47/546; C07C47/55; C07C57/00; C07C57/30; C07C57/42; C07C57/64; C07C57/72; C07C63/00; C07C63/66; C07D295/22; C07D295/26; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/30; C07F9/32; C07F9/3205; C07F9/3241; C07F9/38; C07F9/40; C07F9/4003; C07F9/4056; C07F9/535; C07F9/5352; C07F9/54; C07F9/5456; C08; C08K; C08K5/00; C08K5/0008; C08K5/0041; C09; C09B; C09B23/00; C09B23/14; C09B23/141; C09B23/148; D; D06; D06L; D06L4/00; D06L4/60
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
113 words
A bis-stilbene compound of the formula ##SPC138## wherein A' represents an α-naphthyl, β-naphthyl, pyridyl or 4-diphenylyl radical or a radical of formula ##SPC139## wherein X 1 represents hydrogen, an alkyl group containing 1 to 4 carbon atoms halogen or alkoxy with 1 to 4 carbon atoms, X 2 and X 3 represent hydrogen, an alkyl group containing 1 to 4 carbon atoms, halogen, or alkoxy with 1 to 4 carbon atoms or X 2 together with X 3 forms a methylenedioxy group, M represents a salt-forming cation and Y represents a hydrogen atom, halogen, an alkyl group containing 1 to 4 carbon atoms or an alkoxy group containing 1 to 4 carbon atoms.
Claim 2
Dependent Claim
113 words
A bis-stilbene compound of the formula ##SPC138## wherein A' represents an α-naphthyl, β-naphthyl, pyridyl or 4-diphenylyl radical or a radical of formula ##SPC139## wherein X 1 represents hydrogen, an alkyl group containing 1 to 4 carbon atoms halogen or alkoxy with 1 to 4 carbon atoms, X 2 and X 3 represent hydrogen, an alkyl group containing 1 to 4 carbon atoms, halogen, or alkoxy with 1 to 4 carbon atoms or X 2 together with X 3 forms a methylenedioxy group, M represents a salt-forming cation and Y represents a hydrogen atom, halogen, an alkyl group containing 1 to 4 carbon atoms or an alkoxy group containing 1 to 4 carbon atoms.
Claim 3
Dependent Claim
120 words
A bis-stilbene compound according to claim 1, which corresponds to the formula ##SPC140## wherein A 1 ' represents a β-naphthyl, pyridyl or 4-diphenylyl radical or a radical of formula ##SPC141## wherein X 7 represents hydrogen, an alkyl group containing 1 to 4 carbon atoms fluorine or chlorine or alkoxy with 1 to 4 carbon atoms, X 8 and X 9 represent hydrogen, an alkyl group containing 1 to 4 carbon atoms, fluorine or chlorine and X 8 is also alkoxy with 1 to 4 carbon atoms, M represents a salt-forming cation and Y 1 represents a hydrogen atom, fluorine or chlorine, an alkyl group containing 1 to 4 carbon atoms or an alkoxy group containing 1 to 4 carbon atoms.
Claim 4
Dependent Claim
100 words
A bis-stilbene compound according to claim 2, wherein X 7 denotes hydrogen, methyl, tert. butyl, fluorine, chlorine or alkoxy with 1 to 4 carbon atoms, X 8 denotes hydrogen, methyl, tert, butyl, fluorine, chlorine or alkoxy with 1 to 4 carbon atoms and X 9 denotes hydrogen, methyl, fluorine or chlorine, M represents a salt-forming cation from the group consisting of hydrogen ion, alkali metal ion, ammonium ion or amine salt ion and Y 1 represents a hydrogen atom, fluorine, chlorine, an alkyl group containing 1 to 4 carbon atoms or an alkoxy group containing 1 to 4 carbon atoms.
Claim 5
Dependent Claim
70 words
A bis-stilbene compound according to claim 1, which corresponds to the formula ##SPC142## wherein X 13 denotes hydrogen, methyl, alkoxy with 1 to 4 carbon atoms, or chlorine, X 14 denotes hydrogen, methyl, alkoxy with 1 to 4 carbon atoms or chlorine, X 15 denotes hydrogen or methyl and M 1 represents a salt-forming cation from the group of hydrogen ion, alkali metal ion, ammonium ion or amine salt ion.
Claim 6
Dependent Claim
64 words
A bis-stilbene compound according to claim 1, which corresponds to the formula ##SPC143## wherein R 3 represents hydrogen or methyl, methoxy or chlorine, n denotes the numbers 1 or 2, with R 3 being in the m-position, R 4 denotes hydrogen, fluorine, and M 1 represents a salt-forming cation from the group of hydrogen ion, alkali metal ion, ammonium ion or amine salt ion.
Claim 7
Dependent Claim
17 words
A compound as claimed in claim 1, having the formula ##SPC144## or an alkali metal salt thereof.
Claim 8
Dependent Claim
17 words
A compound as claimed in claim 1, having the formula ##SPC145## or an alkali metal salt thereof.
Claim 9
Dependent Claim
17 words
A compound as claimed in claim 1, having the formula ##SPC146## or an alkali metal salt thereof.
Claim 10
Dependent Claim
17 words
A compound as claimed in claim 1, having the formula ##SPC147## or an alkali metal salt thereof.
Claim 11
Dependent Claim
17 words
A compound as claimed in claim 1, having the formula ##SPC148## or an alkali metal salt thereof.
Claim 12
Dependent Claim
145 words
A symmetrical bis-stilbene compound of the formula ##SPC149## in which V 1 represents hydrogen or a substituent Q representing a member selected from the group consisting of a sulphonic acid group or a salt thereof; V 2 represents hydrogen, an alkyl group with 1 to 18 carbon atoms, an alkoxy group with 1 to 12 carbon atoms, halogen or a sulphonic acid group or a salt thereof; V 3 represents hydrogen or an alkyl group with 1 to 4 carbon atoms; W 1 represents an alkyl group containing 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, halogen, or a substituent Q representing a member selected from the group consisting of a sulphonic acid group or a salt thereof, on condition that at least one of the symbols V 1 or W 1 has the significance of a substituent Q.
Claim 13
Dependent Claim
145 words
A symmetrical bis-stilbene compound of the formula ##SPC149## in which V 1 represents hydrogen or a substituent Q representing a member selected from the group consisting of a sulphonic acid group or a salt thereof; V 2 represents hydrogen, an alkyl group with 1 to 18 carbon atoms, an alkoxy group with 1 to 12 carbon atoms, halogen or a sulphonic acid group or a salt thereof; V 3 represents hydrogen or an alkyl group with 1 to 4 carbon atoms; W 1 represents an alkyl group containing 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, halogen, or a substituent Q representing a member selected from the group consisting of a sulphonic acid group or a salt thereof, on condition that at least one of the symbols V 1 or W 1 has the significance of a substituent Q.
Claim 14
Dependent Claim
48 words
A symmetrical bis-stilbene compound according to claim 11, of the formula ##SPC150## in which one of the symbols U 11 or U 12 is a sulphonic acid group or its salts and the other represents a chlorine atom or an alkyl group with 1 to 4 carbon atoms.
Claim 15
Dependent Claim
52 words
A symmetrical bis-stilbene compound according to claim 11, of the formula ##SPC151## in which U 15 represents a hydrogen or chlorine atom, an alkyl or alkoxy group with up to 4 carbon atoms, and Y is a cation, selected from the group consisting of hydrogen, alkali metal, ammonia, amine, barium and calcium.
Claim 16
Dependent Claim
73 words
A symmetrical bis-stilbene compound of the formula ##SPC152## in which V 1 represents a sulphonic acid group or a salt, or an ester, thereof; V 2 represents hydrogen, an alkyl group with 1 to 18 carbon atoms, an alkoxy group with 1 to 12 carbon atoms, halogen or a sulphonic acid group or a salt, ester thereof, and V 3 stands for hydrogen or an alkyl group with 1 to 4 carbon atoms.
Claim 17
Dependent Claim
73 words
A symmetrical bis-stilbene compound of the formula ##SPC152## in which V 1 represents a sulphonic acid group or a salt, or an ester, thereof; V 2 represents hydrogen, an alkyl group with 1 to 18 carbon atoms, an alkoxy group with 1 to 12 carbon atoms, halogen or a sulphonic acid group or a salt, ester thereof, and V 3 stands for hydrogen or an alkyl group with 1 to 4 carbon atoms.
Claim 18
Dependent Claim
70 words
A symmetrical bis-stilbene compound according to claim 14, wherein V 1 represents a sulphonic acid group or a salt thereof, V 2 represents hydrogen, an alkyl group with 1 to 18 carbon atoms, an alkoxy group with 1 to 12 carbon atoms, halogen or a sulphonic acid group or a salt or ester thereof, and V 3 stands for hydrogen or an alkyl group with 1 to 4 carbon atoms.
Claim 19
Dependent Claim
61 words
A symmetrical bis-stilbene compound according to claim 14, of the formula ##SPC153## in which V 4 represents a sulphonic acid group or a salt or ester thereof; and V 5 represents hydrogen, a sulphonic acid group or a salt or ester thereof; an alkyl group with 1 to 4 carbon atoms or an alkoxy group with 1 to 4 carbon atoms.
Claim 20
Dependent Claim
42 words
A symmetrical bis-stilbene compound according to claim 14, of the formula ##SPC154## in which U 13 represents a sulphonic acid group or its salt and U 14 a hydrogen or chlorine atom or an alkyl group with 1 to 4 carbon atoms.
Claim 21
Dependent Claim
48 words
A symmetrical bis-stilbene compound according to claim 14, of the formula ##SPC155## in which Y represents a cation selected from the group consisting of hydrogen, alkali metal, ammonium, amine, barium and calcium and the YO 3 S-- groups are preferably in the ortho-position relatively to the --CH-- groups.
Claim 22
Dependent Claim
25 words
A symmetrical bis-stilbene compound according to claim 14, of the formula ##SPC156## in which V 6 represents a sulphonic acid group or a salt thereof.
Claim 23
Dependent Claim
17 words
A compound as claimed in claim 14, having the formula ##SPC157## or an alkali metal salt thereof.
Claim 24
Dependent Claim
17 words
A compound as claimed in claim 14, having the formula ##SPC158## or an alkali metal salt thereof.
Claim 25
Dependent Claim
17 words
A compound as claimed in claim 14, having the formula ##SPC159## or an alkali metal salt thereof.
Claim 26
Dependent Claim
17 words
A compound as claimed in claim 14, having the formula ##SPC160## or an alkali metal salt thereof.
References Cited (Backward Citations)
US3177208A
Cited
US3843718A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-10-05 | 1980-04-05 | 1980-10-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-10-05 | 1984-04-05 | 1984-10-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-10-05 | 1988-04-05 | 1988-10-05 | $7700.00 | Window Closed / Lapsed |