US5086086A
Expired / Lapsed
US
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Energy-induced curable compositions
Assignee: 3M Co
•
Filing: 1990-05-02
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Granted: 1992-02-04
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Expires: 2010-05-02
Abstract
Abstract A polymerizable composition comprises a polymeric precursor selected from the group consisting of 1) at least one ethylenically-unsaturated monomer, 2) at least one epoxy monomer, and 3) polyurethane precursors, and a curing agent comprising an organometallic compound and an onium salt.
Inventors
- 👤 Katherine A. Brown-Wensley
- 👤 Robert J. DeVoe
- 👤 Michael C. Palazzotto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 11:32
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/02; C08G65/04; C08G65/06; C08G65/08; C08G65/10; C08G65/12; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50; C08F4/00; C08F4/42; C08F4/44; C08G18/00; C08G18/06; C08G18/08; C08G18/16; C08G18/161; C08G18/22; C08G18/28; C08G18/40; C08G18/63; C08G18/637; C08G59/00; C08G59/18; C08G59/68
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
305 words
A polymerizable composition consisting essentially of a least one ethylenically-unsaturated monomer selected from the group consisting of a) acrylates and methacrylates free of epoxy functionality, b) acrylamides and methacrylamides, and c) vinyl azlactones and divinyl compounds selected from the group consisting of diallyl phthalate, divinyl succinate, divinyl adipate, and divinyl phthalate, and a curing agent comprising an organometallic compound and 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 valence 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 transition metal atom 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
305 words
A polymerizable composition consisting essentially of a least one ethylenically-unsaturated monomer selected from the group consisting of a) acrylates and methacrylates free of epoxy functionality, b) acrylamides and methacrylamides, and c) vinyl azlactones and divinyl compounds selected from the group consisting of diallyl phthalate, divinyl succinate, divinyl adipate, and divinyl phthalate, and a curing agent comprising an organometallic compound and 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 valence 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 transition metal atom 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
9 words
The composition according to claim 1 which is photopolymerizable.
Claim 4
Dependent Claim
19 words
The composition according to claim 1 wherein said at least one ethylenically-unsaturated monomer and said composition is thermally polymerizable.
Claim 5
Dependent Claim
38 words
The composition according to claim 1 wherein said onium salt has the formula II AX II wherein A is an iodonium or sulfonium cation, and X is an organic sulfonate counterion, or a halogenated metal or metalloid counterion.
Claim 6
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 7
Dependent Claim
25 words
The composition according to claim 5 wherein said curing agent is present in the range of 0.1 to 10 weight percent of said total composition.
Claim 8
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 9
Dependent Claim
25 words
The composition according to claim 7 wherein the ratio of organometallic compound to onium salt is in the range of 5:1 to 1:5 by weight.
Claim 10
Dependent Claim
14 words
The composition according to claim 1 wherein said ethylenically-unsaturated monomer is a vinyl compound.
Claim 11
Dependent Claim
13 words
The composition according to claim 9 wherein said ethylenically-unsaturated monomer is an acrylate.
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
28 words
The composition according to claim 1 wherein said organometallic compound is selected from the group consisting of Mn 2 (CO) 8 (1,10-phenanthroline) and (CO) 5 Mn-FeCp(CO) 2 .
Claim 14
Dependent Claim
97 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
72 words
A process comprising the steps of: a) providing a mixture comprising a polymeric precursor selected from the group consisting of at least one ethylenically-unsaturated compound according to claim 1, and b) a catalytically effective amount of a curing agent comprising (1) an organometallic compound according to claim 1, and (2) an onium salt according to claim 1; c) allowing said mixture to polymerize or adding energy to said mixture to effect polymerization.
Claim 16
Dependent Claim
27 words
The method according to claim 14 wherein said energy is at least one of electromagnetic radiation, accelerated particles, or thermal energy for polyurethane precursors and ethylencially-unsaturated compounds.
Claim 17
Dependent Claim
25 words
The method according to claim 14 wherein said polymerizable mixture further comprises up to 90 weight percent of a solvent based on the total mixture.
Claim 18
Dependent Claim
11 words
A cured composition prepared according to the method of claim 14.
Claim 19
Dependent Claim
7 words
A shaped article according to claim 17.
Claim 20
Dependent Claim
19 words
A layered structure comprising a substrate having coated on one surface thereof the polymerizable composition according to claim 1.
Claim 21
Dependent Claim
7 words
The cured structure according to claim 19.
Claim 22
Dependent Claim
12 words
The layered structure according to claim 19 which is an imageable 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
US4086091A
Cited
US4428807A
Cited
US4216288A
Cited
GB2042550A
Cited
US4228232A
Cited
US4250053A
Cited
US4412048A
Cited
EP0094914A2
Cited
EP0094915A2
Cited
EP0109851A2
Cited
US4533446A
Cited
US4521545A
Cited
ZA837966B
Cited
US4593052A
Cited
US4544466A
Cited
US4549945A
Cited
EP0155704A2
Cited
US4525232A
Cited
US4582861A
Cited
EP0207899A2
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) | 1995-02-03 | 1995-08-05 | 1996-02-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-02-03 | 1999-08-05 | 2000-02-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-02-03 | 2003-08-05 | 2004-02-04 | $7700.00 | Window Closed / Lapsed |