EP0515133A2
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EP
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Fluorone and pyronin Y derivatives
Assignee: Spectra Group Ltd Inc
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Filing: 1992-05-19
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Granted: —
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Expires: 2012-05-19
Abstract
Abstract A novel class of compounds is described, certain members of which are useful as fluorescers or as photoinitiators. The compounds have the general structures (I) (II) (III) or (IV): where A is selected from hydrogen, alkyl, aryl, alkenyl, alkynyl, dichlorotriazinylamino, and electron withdrawing groups (EWG) which are stronger electron withdrawing groups than a phenyl group or a halogen-substituted or a carboxyl-substituted phenyl group; X is oxygen, sulfur, selenium, tellurium or >C=0 and preferably oxygen; Z is a counter ion; R is hydrogen, alkyl, aryl or aralkyl; R¹¹-R¹⁶ are the same or different and represent a hydrogen atom or a halogen atom; and R¹⁷ is a hydrogen atom or a group of the formula -OR'. The compounds of formula (I) and (II) may be substituted or unsubstituted at the 2, 4, 5 and 7 positions. When the 2, 4, 5 and 7 positions are unsubstituted, A cannot be hydrogen or methyl.
Inventors
- 👤 Douglas C. Neckers
- 👤 Jianmin Shi
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-30 10:12
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/78; C07D311/80; C07D311/82; C07D311/84; G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/031
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
104 words
A compound of the formula: where A is hydrogen, alkyl, alkenyl, alkynyl, dichlorotriazinylamino, or an electron withdrawing group(EWG) which is more strongly electron withdrawing than a phenyl or a substituted phenyl group, W and W' are respectively selected from O and O⁻, or NR₂⁺ and NR₂, R is hydrogen, lower alkyl, aralkyl, or aryl, and Z is a hydrogen atom or a counter ion, and the compound may be substituted or unsubstituted at the 2, 4, 5 and 7 positions, provided that when A is hydrogen or methyl, the compound is substituted at at least one of the 2, 4, 5, and 7 positions.
Claim 2
Dependent Claim
53 words
A compound according to Claim 1, further characterised in that A is selected from hydrogen, alkenyl, alkynyl, dichlorotriazinylamino, COOR, COR⁵, CONR₂, C(O)OCOR, CN, NO₂, NCS, NCO, SO₂R⁵, SO₃R, SO₂NR₂, CX₃ where R is hydrogen, alkyl, aryl, or aralkyl, X is a halogen atom; and R⁵ is hydrogen, alkyl, aryl, aralkyl, N-imido or NR₂.
Claim 3
Dependent Claim
110 words
A compound according to Claim 2, further characterised in that said compound is represented by the formula (V): where EWG is an electron withdrawing group consisting of A as defined in Claim 2; R¹-R⁴ may be the same or different and are selected from hydrogen, halogen, alkyl, alkenyl, aryl, aralkyl, alkaryl, (CH₂) n COOR⁵, (CH₂) n CONR₂, (CH²) n X, SO₃R, SO₂R⁵, SO₂NR₂, NO₂ , (CH₂) n NR₂, NCO, NCS, (CH₂) n NCO, (CH₂) n NCS, CN, (CH₂) n CN, where n is 1 to 6, and R³ is R⁴ may combine to form a 10 to 12 membered ring; and R⁵ is hydrogen, alkyl, aryl, aralkyl, N-imido or NR₂.
Claim 4
Dependent Claim
16 words
A compound according to Claim 3, further characterised in that R¹ and R² are alkyl groups.
Claim 5
Dependent Claim
23 words
A compound according to Claim 3, further characterised in that R¹ and R² are alkyl groups, W is NR₂⁺ and W' is NR₂.
Claim 6
Dependent Claim
23 words
A compound according to Claim 3, further characterised in that R¹ and R² are alkyl groups, W is O and W' is O-.
Claim 7
Dependent Claim
18 words
A compound according to any of Claims 1, 5 or 6, further characterised in that EWG is CN.
Claim 8
Dependent Claim
13 words
A compound according to Claim 3, further characterised in that EWG is CF₃.
Claim 9
Dependent Claim
28 words
A compound according to Claim 3, further characterised in that R³ and/or R⁴ includes a functional group suitable for coupling said compound to a ligand-analog or an antibody.
Claim 10
Dependent Claim
17 words
A compound according to Claim 9, further characterised in that said functional group is COOR⁵ or NR₂.
Claim 11
Dependent Claim
19 words
A compound according to Claim 10, further characterised in that said functional group is oxalyl, sulfonyl, N-imido or carboamidosulfonyl.
Claim 12
Dependent Claim
26 words
A compound according to Claim 3, further characterised in that at least one of R¹-R⁴ includes a functional group which products intramolecular ionization of said compound.
Claim 13
Dependent Claim
37 words
A compound according to Claim 3, further characterised in that A is hydrogen and one of R¹-R⁴ is CN, NCO, NCS, (CH₂) n CN, (CH₂) n NCO and (CH₂) n NCS where n is 1 to 6.
Claim 14
Dependent Claim
20 words
A compound according to any preceding claim, further characterised in that said compound fluoresces upon the absorption of actinic radiation.
Claim 15
Dependent Claim
31 words
A compound according to any of Claims 1 to 13, wherein said compound is capable of generating free radicals upon absorption of actinic radiation alone or in combination with a coinitiator.
Claim 16
Dependent Claim
113 words
A compound of the formula (X): where A is selected from hydrogen, alkenyl, alkynyl, dichlorotriazinylamino, COOR, COR⁵, CONR₂, C(O)OCOR, CN, NO₂, NCS, NCO, SO₂R⁵, SO₃R, SO₂NR₂, CX₃ where R is hydrogen, alkyl, aryl, or aralkyl and X may be the same or different and is a halogen atom; W and W' are selected from either O and O-, or NR₂+ and NR₂; R⁵ is hydrogen, alkyl, aryl, aralkyl, N-imido or NR₂; and A' represents a ligand-analog or an antibody and Y is a linking group and the A'(Y) moiety may be at one of the 2, 4, 5, 7 or 9 positions and the balance of those positions may be substituted or unsubstituted.
Claim 17
Dependent Claim
97 words
A composition for detecting oil leakage comprising an oil vehicle and a fluorescent dye, characterised in that said dye is a compound of the formula: where EWG is an electron withdrawing group which is more strongly electron withdrawing than a phenyl or a halogen or carboxyl substituted phenyl group, W and W' are O and O⁻ or NR₂⁺ and NR₂, R is hydrogen, alkyl, aralkyl, or aryl, Z is a hydrogen atom or a counter ion, and the compound is substituted with an oleophilic moiety at at least one of the 2, 4, 5 and 7 positions.
Claim 18
Dependent Claim
77 words
A compound of the formula (III) or (IV) where X is oxygen, sulfur, selenium, tellurium, or C=0, A is hydrogen, alkenyl, aryl, or an electron withdrawing group selected from quaternary amino, nitro, nitroso, cyano, -SO₃R', -SO₂R', halogen, trihalomethyl, -CHO, carbamoyl, sulfamoyl, sulfinyl and -COOR' where R' is hydrogen, alkyl, aryl, or aralkyl; and R¹¹-R¹⁶ are the same or different and represent a hydrogen or a halogen atom; and R¹⁷ is a hydrogen atom or an -OR' group.
Claim 19
Dependent Claim
18 words
A compound according to Claim 18, further characterised in that said fluorone is represented by the formula VI
Claim 20
Dependent Claim
17 words
A compound according to Claim 19, further characterised in that A is hydrogen and R¹¹-R¹⁴ are bromine.
Claim 21
Dependent Claim
16 words
A compound according to Claim 19, further characterised in that it is useful as a photoinitiator.
References Cited (Backward Citations)
No citation records indexed.
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