Claims
- 1. A photohardenable composition comprising a polymerizable compound and a compound of the formula I or II ##STR13## where R.sup.1, R.sup.2, R.sup.5 and R.sup.6 are the same or different and represent a hydrogen atom or a halogen atom and R.sup.1 and R.sup.2 can combine to form a ring; R.sup.3 and R.sup.4 are the same or different and represent a hydrogen atom, a halogen atom, a benzoyl group, a group of the formula --L(CH.sub.2).sub.n R.sup.8 where n is 1 to 8, R.sup.8 is hydrogen, hydroxy, amino, dialkylamino, --COR.sup.16 or --COOR.sup.14 where R.sup.16 is hydrogen, chlorine, COCl, C1-C8 alkyl, NR.sub.2 or aryl and R.sup.14 is hydrogen, C1-C8 alkyl, aryl, COR, 2,4-dinitrophenyl, N-imido or NR.sub.2 and L is a direct bond or >C.dbd.O, provided that at least two of R.sup.1 -R.sup.6 are iodo or bromo; W is .dbd.O or .dbd.NR.sub.2 +Z-- where R is hydrogen or lower alkyl, Z is a counter ion, when W is .dbd.O, W.sup.1 is hydrogen or --OR.sup.9 where R.sup.9 is hydrogen, C1-C8 alkyl, acyl or a group of the formula --(CH.sub.2).sub.n R.sup.10 where n is 1 to 8 and R.sup.10 is amino, dialkylamino, hydroxy, acryloyl or methacryloyl and when W is .dbd.NR.sub.2 +Z--, W.sup.1 is hydrogen or --NR.sub.2 ; Y is oxygen, sulfur, selenium, tellurium, >C.dbd.O, or N--R.sup.13 where R.sup.13 is 4-methylphenyl, A is hydrogen, alkenyl, alkyl, or an electron withdrawing group (EWG) selected from the group consisting of COOR.sup.11, COR.sup.12, C(O)OCOR.sup.11, CONR.sub.2, CN, NO.sub.2, NCS, NCO, SO.sub.2 R.sup.12, SO.sub.3 R.sup.11, SO.sub.2 NR.sub.2, CX.sub.3.sup.2 ; R.sup.11 is hydrogen, alkyl, aryl, or aralkyl R.sup.12 is hydrogen, alkyl, aryl, or aralkyl, X.sup.2 can be the same or different and is a halogen atom.
- 2. The composition of claim 1 wherein said compound is represented by the Formula (I).
- 3. The composition of claim 2 wherein said compound is represented by the Formula (III) or (IV) ##STR14## where Y.sup.1 is oxygen, sulfur or >NR.sup.13.
- 4. The composition of claim 3 wherein X.sup.1 is 0.
- 5. The composition of claim 4 wherein said compound is represented by the Formula (III).
- 6. The composition of claim 5 wherein A is hydrogen.
- 7. The composition of claim 5 wherein A is CN.
- 8. The composition of claim 5 wherein said composition includes a coinitiator capable of accepting an electron from or donating an electron to said compound.
- 9. The composition of claim 8 wherein said conitiator is N-phenylglycine or an N,N-dialkylaniline.
- 10. 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.
- 11. The composition of claim 10 wherein said composition additionally includes an onium salt.
- 12. The composition of claim 11 wherein said composition includes a diphenyliodonium salt.
- 13. The composition of claim 5 wherein R.sup.10 is acryloyl or methacryloyl.
Parent Case Info
This application is a combined continuation-in-part of U.S. application Ser. No. 07/881,048 filed May 11, 1992, now abandoned and Ser. No. 07/772,103 filed Oct. 7, 1991, now abandoned which in turn is a continuation-in-part of Ser. No. 07/756,611 filed Sep. 9, 1991 now abandoned, which in turn is a continuation-in-part of Ser. No. 07/702,886 filed May 20, 1991 now abandoned.
US Referenced Citations (14)
Foreign Referenced Citations (1)
Number |
Date |
Country |
9010254 |
Sep 1990 |
EPX |
Continuation in Parts (3)
|
Number |
Date |
Country |
Parent |
881048 |
May 1992 |
|
Parent |
756611 |
Sep 1991 |
|
Parent |
702886 |
May 1991 |
|