US4713401A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Titanocenes and a radiation-polymerizable composition containing these titanocenes
Assignee: BASF Corp
•
Filing: 1985-12-11
•
Granted: 1987-12-15
•
Expires: 2005-12-11
Abstract
Abstract Titanocenes with π-cyclopentadienyl ligands, in which one or two carbocyclic or heterocyclic aromatic rings are bonded to the metal, the aromatic rings being substituted in at least one of the two ortho-positions relative to the metal-carbon bonds by CF 2 Z (Z=F or substituted or unsubstituted alkyl), are suitable as photoinitiators for the photopolymerization of ethylenically unsaturated compounds. They are distinguished by a high radiation sensitivity, stability to air and thermal effects, and high effectiveness in the range from UV light to visible light.
Inventors
- 👤 Martin Riediker
- 👤 Kurt Meier
- 👤 Hans Zweifel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 18:25
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/029; C; C07; C07F; C07F17/00; C07F7/00; C07F7/28; C08; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/126; Y10S430/148
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
192 words
A composition which is polymerizable upon irradiation which comprises (a) at least one non-volatile monomeric, oligomeric or polymeric compound having at least one polymerizable ehtyleneically unsaturated double bond, and (b) as photoinitiator, an effective amount of at least one titanocene of formula I ##STR42## in which the two R 1 idependently of one another are unsubstituted or substituted cyclopentadienyl.sup.⊖, indenyl.sup.⊖ or 4,5, 6,7-tetrahydroindenyl.sup.⊖, or both R 1 together are an unsubstituted or substituted radical of the formula II ##STR43## in which X is --(CH 2 ) n with n=1, 2 or 3, alkylidene having 2 to 12 C atoms, cycloalkylidene having 5 to 7 ring carbon atoms, SiR 2 4 or SnR 2 4 , and R 4 is C 1 -C 12 -alkyl, C 5 -C 12 -cycloalkyl, C 6 -C 16 -aryl or C 7 -C 16 -aralkyl, R 2 is a 6-membered carbocyclic aromatic ring which is substituted in at least one of the two ortho-positions relative to the metal-carbon bond by --CF 2 Z, in which Z is F or unsubstituted or substituted alkyl, or and R 3 is as defined for R 2 or is halogen, pseudohalogen.
Claim 2
Dependent Claim
192 words
A composition which is polymerizable upon irradiation which comprises (a) at least one non-volatile monomeric, oligomeric or polymeric compound having at least one polymerizable ehtyleneically unsaturated double bond, and (b) as photoinitiator, an effective amount of at least one titanocene of formula I ##STR42## in which the two R 1 idependently of one another are unsubstituted or substituted cyclopentadienyl.sup.⊖, indenyl.sup.⊖ or 4,5, 6,7-tetrahydroindenyl.sup.⊖, or both R 1 together are an unsubstituted or substituted radical of the formula II ##STR43## in which X is --(CH 2 ) n with n=1, 2 or 3, alkylidene having 2 to 12 C atoms, cycloalkylidene having 5 to 7 ring carbon atoms, SiR 2 4 or SnR 2 4 , and R 4 is C 1 -C 12 -alkyl, C 5 -C 12 -cycloalkyl, C 6 -C 16 -aryl or C 7 -C 16 -aralkyl, R 2 is a 6-membered carbocyclic aromatic ring which is substituted in at least one of the two ortho-positions relative to the metal-carbon bond by --CF 2 Z, in which Z is F or unsubstituted or substituted alkyl, or and R 3 is as defined for R 2 or is halogen, pseudohalogen.
Claim 3
Dependent Claim
38 words
A composition according to claim 1 where in the titanocene of formula I of component (b) R 1 is substituted by alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkoxy, cyano, halogen, amino or aminoalkyl or quaternized amino or aminoalkyl.
Claim 4
Dependent Claim
41 words
A composition according to claim 1 where in the titanocene of formula I of component (b) R 2 is further substituted by alkyl, cycloalkyl, aryl, aralkyl, hydroxyl, alkoxy, carboxyl, alkoxycarbonyl, aminocarbonyl, halogen, CN, amino or aminoalkyl or quaternized amino or aminoalkyl.
Claim 5
Dependent Claim
22 words
A composition according to claim 1 wherein in the titanocene of formula I of component (b) R 1 is cyclopentadienyl.sup.⊖ or methylcyclopentadienyl.sup.⊖.
Claim 6
Dependent Claim
45 words
A composition according to claim 3 wherein in the titanocene of formula I of component (b) R 2 is a radical of formula III ##STR44## in which R 5 , R 6 , R 7 and R 8 are independently hydrogen, bromine, chlorine or fluorine.
Claim 7
Dependent Claim
44 words
A composition according to claim 5 where in the titanocene of component (b) R 5 , R 6 and R 7 are hydrogen atoms, and R 8 is bonded in the ortho-position relative to the free bond and is fluorine or a hydrogen atom.
Claim 8
Dependent Claim
41 words
A composition according to claim 1 where in the titanocene of formula I of component (b) R 1 is cyclopentadienyl.sup.⊖ or methylcyclopentadienyl.sup.⊖, R 2 is ##STR45## R 8 is hydrogen, chlorine or fluorine, and R 3 is defined in claim 1.
Claim 9
Dependent Claim
22 words
A composition according to claim 7 where in the titanocene of formula I of component (b) R 3 is halogen or pseudohalogen.
Claim 10
Dependent Claim
29 words
A composition according to claim 8 where in the titanocene of formula I of component (b) R 3 is F, Cl, Br, N 3 , CN, NCO or NCS.
Claim 11
Dependent Claim
19 words
A coated substrate which contains, on at least one surface, a layer of a composition according to claim 1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-12-14 | 1991-06-15 | 1991-12-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-12-14 | 1995-06-15 | 1995-12-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-12-14 | 1999-06-15 | 1999-12-15 | $7700.00 | Window Closed / Lapsed |