Patent US4950696A successfully refreshed from Google Patents.
US4950696A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Energy-induced dual curable compositions
Assignee: 3M Co
•
Filing: 1987-08-28
•
Granted: 1990-08-21
•
Expires: 2007-08-28
Abstract
Abstract An energy polymerizable composition comprises at least one ethylenically-unsaturated monomer, one of polyurethane precursors, and at least one epoxy monomer, and a curing agent comprising an organometallic compound, and an onium salt.
Inventors
- 👤 Michael C. Palazotto
- 👤 Katherine A. Brown-Wensley
- 👤 Robert J. DeVoe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 20:03
CPC Classifications
C; C08; C08F; C08F4/00; C08F4/42; C08F4/44; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/58; C08F2/00; C08F2/46; C08F2/48; C08F2/50; C08G18/08; C08G18/16; C08G18/161; C08G18/22; C08G18/63; C08G18/637; C08G59/00; C08G59/18; C08G59/68; C08G65/00; C08G65/02; C08G65/04; C08G65/06; C08G65/08; C08G65/10; C08G65/12; Y; Y10; Y10S; Y10S428/00; Y10S428/90; Y10S428/901; Y10S428/922; Y10S428/9265; Y10S428/928; Y10S428/932; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/115; Y10S430/122; Y10S430/124; Y10T; Y10T428/00; Y10T428/24; Y10T428/24355; Y10T428/24372; Y10T428/24802; Y10T428/24835; Y10T428/24893; Y10T428/24917
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
308 words
An energy polymerizable composition comprising (a) at least one ethylenically-unsaturated monomer different from each (b) precursor, (b) polyurethane precursors, said polyurethane precursors comprising at least an additional different monomer which is one monomer having at least two isocyanate groups and at least one monomer having at least two isocyanate-reactive hydrogen atoms, and (c) a curing agent comprising (1) an organometallic compound, and (2) an onium salt selected from the group consisting of halonium compounds and cationic compounds of hypervalent Group VIA elements said organometallic compound having the formula, L.sup.1 L.sup.2 L.sup.3 M wherein L 1 represents none, or 1 to 12 ligands contributing pi-electrons that can be the same or different ligand selected from substituted and unsubstituted acyclic and cyclic unsaturated compounds and groups and substituted and unsubstituted carbocyclic aromatic and heterocyclic aromatic compounds, each capable of contributing 2 to 24 pi-electrons to the valence shell of M; L 2 represents none, or 1 to 24 ligands that can be the same or different contributing an even number of sigma-electrons selected from mono-, di-, and tri- dentate ligands, each donating 2, 4, or 6 sigma-electrons to the valece shell of M; L 3 represents none, or 1 to 12 ligands that can be the same or different, each contributing no more than one sigma-electron each to the valence shell of each M; Ligands L 1 , L 2 , and L 3 can be bridging or non-bridging ligands; M represents 1 to 4 of the same or different metal atoms selected from the elements of Periodic Groups IVB, VB, VIB, VIIB, and VIIIB; with the proviso that said organometallic compound contains at least one of a metal-metal sigma bond and L 3 ; and with the proviso that L 1 , L 2 , L 3 , and M are chosen so as to achieve a stable configuration.
Claim 2
Dependent Claim
308 words
An energy polymerizable composition comprising (a) at least one ethylenically-unsaturated monomer different from each (b) precursor, (b) polyurethane precursors, said polyurethane precursors comprising at least an additional different monomer which is one monomer having at least two isocyanate groups and at least one monomer having at least two isocyanate-reactive hydrogen atoms, and (c) a curing agent comprising (1) an organometallic compound, and (2) an onium salt selected from the group consisting of halonium compounds and cationic compounds of hypervalent Group VIA elements said organometallic compound having the formula, L.sup.1 L.sup.2 L.sup.3 M wherein L 1 represents none, or 1 to 12 ligands contributing pi-electrons that can be the same or different ligand selected from substituted and unsubstituted acyclic and cyclic unsaturated compounds and groups and substituted and unsubstituted carbocyclic aromatic and heterocyclic aromatic compounds, each capable of contributing 2 to 24 pi-electrons to the valence shell of M; L 2 represents none, or 1 to 24 ligands that can be the same or different contributing an even number of sigma-electrons selected from mono-, di-, and tri- dentate ligands, each donating 2, 4, or 6 sigma-electrons to the valece shell of M; L 3 represents none, or 1 to 12 ligands that can be the same or different, each contributing no more than one sigma-electron each to the valence shell of each M; Ligands L 1 , L 2 , and L 3 can be bridging or non-bridging ligands; M represents 1 to 4 of the same or different metal atoms selected from the elements of Periodic Groups IVB, VB, VIB, VIIB, and VIIIB; with the proviso that said organometallic compound contains at least one of a metal-metal sigma bond and L 3 ; and with the proviso that L 1 , L 2 , L 3 , and M are chosen so as to achieve a stable configuration.
Claim 3
Dependent Claim
37 words
The composition according to claim 1 wherein said onium salt has the formula II AX II wherein A is an iodonium or sulfonium, and X is an organic sulfonate counterion, or a halogenated metal or metalloid counterion.
Claim 4
Dependent Claim
24 words
The composition according to claim 1 wherein the ratio of ethylenically-unsaturated monomer to said polyurethane precursors is in the range of 99:1 to 1:99.
Claim 5
Dependent Claim
25 words
The composition according to claim 1 wherein said curing agent is present in the range of 0.1 to 20 weight percent of the total composition.
Claim 6
Dependent Claim
25 words
The composition according to claim 4 wherein said curing agent is present in the range of 0.1 to 10 weight percent of said total composition.
Claim 7
Dependent Claim
29 words
The composition according to claim 1 wherein the ratio of organometallic compound to onium salt of said curing agent is in the range of 10:1 to 1:10 by weight.
Claim 8
Dependent Claim
25 words
The composition according to claim 6 wherein the ratio of organometallic compound to onium salt is in the range of 5:1 to 1:5 by weight.
Claim 9
Dependent Claim
22 words
The composition according to claim 1 wherein said ethylenically-unsaturated monomer is selected from the group consisting of acrylates, acrylamide and vinyl compounds.
Claim 10
Dependent Claim
13 words
The composition according to claim 8 wherein said ethylenically-unsaturated monomer is an acrylate.
Claim 11
Dependent Claim
41 words
The composition according to claim 1 wherein said polyurethane precursors comprise a mixture of polyisocyanates and compounds bearing at least two isocyanate-reactive hydrogen atoms where the ratio of isocyanate groups to isocyanate-reactive hydrogen atoms is in the range 1:2 to 2:1.
Claim 12
Dependent Claim
32 words
The composition according to claim 1 wherein said organometallic compound is selected from the group consisting of [CpFe(CO) 2 ] 2 , Mn 2 (CO) 10 , CpPt(CH 3 ) 3 .
Claim 13
Dependent Claim
16 words
The composition according to claim 1 wherein said organometallic compound is Mn 2 (CO) 8 (1,10-phenanthrolin).
Claim 14
Dependent Claim
95 words
The composition according to claim 1 wherein said onium salt is at least one of Ph 2 I + PF 6 - , Ph 2 I + SbF 6 - , Ph 2 I + AsF 6 - , Ph 2 I + SbF 5 (OH) - , Ph 3 S + PF 6 - , Ph 3 S + SbF 6 - , Ph 3 S + AsF 6 - , PhSC 6 H 4 Sph 2 SbF 6 , and Ph 3 S + SbF 5 (OH) - , wherein Ph is phenyl.
Claim 15
Dependent Claim
10 words
The composition according to claim 1 which has been cured.
Claim 16
Dependent Claim
10 words
An article comprising the cured composition according to claim 14.
Claim 17
Dependent Claim
19 words
A layered structure comprising a substrate having coated on one surface thereof the polymerizable composition according to claim 1.
Claim 18
Dependent Claim
7 words
The cured structure according to claim 16.
Claim 19
Dependent Claim
12 words
The layered structure according to claim 16 which is an imagable structure.
References Cited (Backward Citations)
US3867354A
Cited
US4080274A
Cited
US3705129A
Cited
US4001015A
Cited
US3709861A
Cited
US3794576A
Cited
US3729313A
Cited
US3808006A
Cited
US3714006A
Cited
US3741769A
Cited
US4053316A
Cited
US4113497A
Cited
US4010289A
Cited
US4058400A
Cited
US4026705A
Cited
US4237242A
Cited
US4342793A
Cited
US4086091A
Cited
US4156035A
Cited
US4428807A
Cited
US4216288A
Cited
GB2042550A
Cited
US4228232A
Cited
US4250053A
Cited
US4227978A
Cited
US4412048A
Cited
EP0094915A2
Cited
EP0094914A2
Cited
EP0109851A2
Cited
US4533446A
Cited
US4521545A
Cited
ZA837966B
Cited
US4593052A
Cited
US4544466A
Cited
US4549945A
Cited
EP0155704A2
Cited
US4525232A
Cited
US4582861A
Cited
US4623676A
Cited
EP0207893A2
Cited
US4707432A
Cited
US4734444A
Cited
US4657779A
Cited
US4849320A
Cited
US4740577A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-08-20 | 1994-02-19 | 1994-08-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-08-20 | 1998-02-19 | 1998-08-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-08-20 | 2002-02-19 | 2002-08-21 | $7700.00 | Window Closed / Lapsed |