US5451343A
Expired / Lapsed
US
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Fluorone and pyronin y derivatives
Assignee: Spectra Group Ltd Inc
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Filing: 1993-11-19
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Granted: 1995-09-19
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Expires: 2013-11-19
Abstract
Abstract The present invention relates to a novel class of compounds which absorb light at wavelengths greater than 350 nm and are useful as fluorescers or as photoinitiators. The present invention provides compounds of the formulas (I) and (II) and their equivalents (the nomenclature of the compounds used herein is based on the numbering of positions as shown in formula (I)): ##STR1## where: when W is ═O, W 1 is hydrogen or --OR 9 and when W is ═NR + 2 , W is hydrogen or NR 2 +2 , A is hydrogen, alkenyl, alkyl or an election withdrawing group, and the remaining groups are as defined in the disclosure.
Inventors
- 👤 Douglas C. Neckers
- 👤 Jianmin Shi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 05:49
CPC Classifications
C; C08; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50; C07; C07D; C07D311/00; C07D311/02; C07D311/78; C07D311/80; C07D311/82; C07D311/84; C08G; C08G59/00; C08G59/18; C08G59/68; C09; C09B; C09B11/00; C09B11/04; C09B11/10; C09B11/24; C09B11/28; G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/029; G03F7/031; G03F7/038; G03F7/075; G03F7/0755; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/115; Y10S430/122; Y10S430/124; Y10S430/126
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
333 words
A photohardenable composition comprising a polymerizable compound and a compound of the formula I or II ##STR13## where R 1 , R 2 , R 5 and R 6 are the same or different and represent a hydrogen atom or a halogen atom and R 1 and R 2 can combine to form a ring; R 3 and R 4 are the same or different and represent a hydrogen atom, a halogen atom, a benzoyl group, a group of the formula --L(CH 2 ) n R 8 where n is 1 to 8, R 8 is hydrogen, hydroxy, amino, dialkylamino, --COR 16 or --COOR 14 where R 16 is hydrogen, chlorine, COCl, C1-C8 alkyl, NR 2 or aryl and R 14 is hydrogen, C1-C8 alkyl, aryl, COR, 2,4-dinitrophenyl, N-imido or NR 2 and L is a direct bond or >C═O, provided that at least two of R 1 -R 6 are iodo or bromo; W is ═O or ═NR 2 +Z-- where R is hydrogen or lower alkyl, Z is a counter ion, when W is ═O, W 1 is hydrogen or --OR 9 where R 9 is hydrogen, C1-C8 alkyl, acyl or a group of the formula --(CH 2 ) n R 10 where n is 1 to 8 and R 10 is amino, dialkylamino, hydroxy, acryloyl or methacryloyl and when W is ═NR 2 +Z--, W 1 is hydrogen or --NR 2 ; Y is oxygen, sulfur, selenium, tellurium, >C═O, or N--R 13 where R 13 is 4-methylphenyl, A is hydrogen, alkenyl, alkyl, or an electron withdrawing group (EWG) selected from the group consisting of COOR 11 , COR 12 , C(O)OCOR 11 , CONR 2 , CN, NO 2 , NCS, NCO, SO 2 R 12 , SO 3 R 11 , SO 2 NR 2 , CX 3 2 ; R 11 is hydrogen, alkyl, aryl, or aralkyl R 12 is hydrogen, alkyl, aryl, or aralkyl, X 2 can be the same or different and is a halogen atom.
Claim 2
Dependent Claim
333 words
A photohardenable composition comprising a polymerizable compound and a compound of the formula I or II ##STR13## where R 1 , R 2 , R 5 and R 6 are the same or different and represent a hydrogen atom or a halogen atom and R 1 and R 2 can combine to form a ring; R 3 and R 4 are the same or different and represent a hydrogen atom, a halogen atom, a benzoyl group, a group of the formula --L(CH 2 ) n R 8 where n is 1 to 8, R 8 is hydrogen, hydroxy, amino, dialkylamino, --COR 16 or --COOR 14 where R 16 is hydrogen, chlorine, COCl, C1-C8 alkyl, NR 2 or aryl and R 14 is hydrogen, C1-C8 alkyl, aryl, COR, 2,4-dinitrophenyl, N-imido or NR 2 and L is a direct bond or >C═O, provided that at least two of R 1 -R 6 are iodo or bromo; W is ═O or ═NR 2 +Z-- where R is hydrogen or lower alkyl, Z is a counter ion, when W is ═O, W 1 is hydrogen or --OR 9 where R 9 is hydrogen, C1-C8 alkyl, acyl or a group of the formula --(CH 2 ) n R 10 where n is 1 to 8 and R 10 is amino, dialkylamino, hydroxy, acryloyl or methacryloyl and when W is ═NR 2 +Z--, W 1 is hydrogen or --NR 2 ; Y is oxygen, sulfur, selenium, tellurium, >C═O, or N--R 13 where R 13 is 4-methylphenyl, A is hydrogen, alkenyl, alkyl, or an electron withdrawing group (EWG) selected from the group consisting of COOR 11 , COR 12 , C(O)OCOR 11 , CONR 2 , CN, NO 2 , NCS, NCO, SO 2 R 12 , SO 3 R 11 , SO 2 NR 2 , CX 3 2 ; R 11 is hydrogen, alkyl, aryl, or aralkyl R 12 is hydrogen, alkyl, aryl, or aralkyl, X 2 can be the same or different and is a halogen atom.
Claim 3
Dependent Claim
14 words
The composition of claim 1 wherein said compound is represented by the Formula (I).
Claim 4
Dependent Claim
27 words
The composition of claim 2 wherein said compound is represented by the Formula (III) or (IV) ##STR14## where Y 1 is oxygen, sulfur or >NR 13 .
Claim 5
Dependent Claim
10 words
The composition of claim 3 wherein X 1 is 0.
Claim 6
Dependent Claim
14 words
The composition of claim 4 wherein said compound is represented by the Formula (III).
Claim 7
Dependent Claim
9 words
The composition of claim 5 wherein A is hydrogen.
Claim 8
Dependent Claim
9 words
The composition of claim 5 wherein A is CN.
Claim 9
Dependent Claim
24 words
The composition of claim 5 wherein said composition includes a coinitiator capable of accepting an electron from or donating an electron to said compound.
Claim 10
Dependent Claim
13 words
The composition of claim 8 wherein said conitiator is N-phenylglycine or an N,N-dialkylaniline.
Claim 11
Dependent Claim
62 words
The composition of claim 9 wherein said compound is selected from the group consisting of 5,7-diiodo-3-methoxy-6-fluorone (DIMF), 5,7-diiodo-3-ethoxy-6-fluorone (DIEF), 5,7-diiodo-3-butoxy-6-fluorone (DIBF), 5,7-diiodo-3-octoxy-6-fluorone (DIOF), 4,5-diiodo-3-hydroxy-6-fluorone, 9-cyano-5,7-diiodo-3-methoxy-6-fluorone (CDIMF), 9-cyano-5,7-diiodo-3-ethoxy-6-fluorone (CDIEF), 9-cyano-5,7-diiodo-3-butoxy-6-fluoorone (CDIBF), 9-cyano-5,7-diiodo-3-octoxy-6-fluorone (CDIOF), 3-hydroxy-2,4,5,7-tetraiodo-6-fluorone (TIHF), 3-hydroxy-2,4,5,7-tetrabromo-6-fluorone (TBHF), 3-hydroxy-2,4,5,7-tetrachloro-6-fluorone (TCHF), 3-hydroxy-2,4,5,7-tetrafluoro-6-fluorone (TFHF), 9-cyano-3-hydroxy-2,4,5,7-tetraiodo-6-fluorone (TIHCF), 9-cyano-3-hydroxy-2,4,5,7-tetrabromo-6-fluorone (TBHCF), 9-cyano-3-hydroxy-2,4,5,7-tetrachloro-6-fluorone (TCHCF), 9-cyano-3-hydroxy-2,4,5,7-tetrafluoro-6-fluorone (TFHCF), 3-hydroxy-4,5,7-triiodo-2octanoyl-6-fluorone, 9-cyano-3-hydroxy-4,5,7-triiodo-2-octanoyl-6-fluorone, 3-hydroxy-4,5,7-triiodo-2-octanoyl-6-fluorone, 9-cyano-3-hydroxy-4,5,7-triiodo-2-octyl-6-fluorone, 3-hydroxy-2,4,5,7-tetraiodo-6-thiafluorone, 3-hydroxy-4,5,7-triiodo-2-pentanoyl-6-fluorone, 9-cyano-3-hydroxy-4,5,7-triiodo-2-pentanoyl-6-fluorone, 3-hydroxy-4,5,7-triiodo-2-pentyl-6-fluorone, 9-cyano-3-hydroxy-4,5,7-triiodo-2-pentyl-6-fluorone, 2,7-di-t-butyl-4,5-diiodo-3-hydroxy-6-fluorone, 9-cyano-2,7-di-t-butyl-4,5-diiodo-3-hydroxy-6-fluorone, 7-benzoyl-2,4,5-triiodo-3-hydroxy-6-fluorone, 9-cyano-3-hydroxy-7-butyroyl chloride-6-fluorone.
Claim 12
Dependent Claim
13 words
The composition of claim 10 wherein said composition additionally includes an onium salt.
Claim 13
Dependent Claim
12 words
The composition of claim 11 wherein said composition includes a diphenyliodonium salt.
Claim 14
Dependent Claim
12 words
The composition of claim 5 wherein R 10 is acryloyl or methacryloyl.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1998-09-18 | 1999-03-20 | 1999-09-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-09-18 | 2003-03-20 | 2003-09-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-09-18 | 2007-03-20 | 2007-09-19 | $7700.00 | Window Closed / Lapsed |