US5494943A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Stabilized cationically-curable compositions
Assignee: 3M Co
•
Filing: 1993-06-16
•
Granted: 1996-02-27
•
Expires: 2013-06-16
Abstract
Abstract The present invention provides an energy polymerizable composition comprising at least one epoxy monomer or at least one vinyl ether monomer and an initiation system therefor, the initiation system comprising at least one organometallic complex salt and at least one stabilizing additive. The cured composition provides useful articles or coated articles.
Inventors
- 👤 Wayne S. Mahoney
- 👤 Michael C. Palazzotto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 17:36
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/0042; G03F7/0043; C; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G65/00; C08G65/02; C08G65/04; C08G65/06; C08G65/08; C08G65/10; C08G65/105; C08G65/12; G03F7/0045; G03F7/027; G03F7/028; G03F7/029; G03F7/031; G03F7/038; C08G2650/00; C08G2650/02; C08G2650/16; Y; Y10; Y10T; Y10T428/00; Y10T428/28; Y10T428/2809; Y10T428/2852; Y10T428/31504; Y10T428/31511
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
376 words
An energy polymerizable composition comprising a) at least one cationically curable monomer selected from the group consisting of epoxy monomers and vinyl ether-containing monomers, b) a two-component initiator comprising (1) at least one salt of an organometallic complex cation wherein said cation contains at least one carbon atom bonded to a transition metal atom, and (2) at least one stabilizing additive, or an active portion thereof, selected from the group consisting of classes 1 to 5: wherein Class 1 comprises compounds represented by formula III R.sup.1 --Z.sup.1 --R.sup.1 (III) where Z 1 is a diradical moiety selected from the group consisting of ##STR29## and each R 1 independently is a group selected from C 1 to C 10 alkyl groups and groups having 1 to 4 fused or unfused aromatic rings, and the R 1 s together can form a heterocyclic ring having 5 to 7 ring atoms; Class 2 comprises macrocyclic compounds represented by formula IV ##STR30## wherein Z 2 is a diradical --O--, --S--, or --NH--; wherein each R 2 independently can be hydrogen or it can be R 1 as previously defined, or two R 2 s together can form at least one ring which is saturated or unsaturated and the ring can be substituted or unsubstituted with alkyl, alkenyl or alkynyl groups containing from 1 to 30 carbon atoms; the carbon atoms can be interrupted with up to 10 individual, non-catenated heteroatoms selected from O, S, and N; x is 1 or 2, and bis an integer from 3 to 10; Class 3 is represented by compounds having formulae V and VI, ##STR31## wherein each R 2 independently is as previously defined; and a class of tripyridyltriazines ##STR32## wherein each R 2 independently is as previously defined; Class 4 is described by compounds of formula VII: ##STR33## where Z 3 is nitrogen, phosphorus, arsenic or antimony; where each R 1 independently is as defined above, and R 3 can be R 1 or a difunctional group selected from alkylene and phenylene groups, wherein c is either 1 or 2; Class 5 describes Schiff bases and can be represented by compounds of formula VIII: ##STR34## wherein R 2 and R 3 independently are as previously defined, and wherein d is 1 or 2.
Claim 2
Dependent Claim
376 words
An energy polymerizable composition comprising a) at least one cationically curable monomer selected from the group consisting of epoxy monomers and vinyl ether-containing monomers, b) a two-component initiator comprising (1) at least one salt of an organometallic complex cation wherein said cation contains at least one carbon atom bonded to a transition metal atom, and (2) at least one stabilizing additive, or an active portion thereof, selected from the group consisting of classes 1 to 5: wherein Class 1 comprises compounds represented by formula III R.sup.1 --Z.sup.1 --R.sup.1 (III) where Z 1 is a diradical moiety selected from the group consisting of ##STR29## and each R 1 independently is a group selected from C 1 to C 10 alkyl groups and groups having 1 to 4 fused or unfused aromatic rings, and the R 1 s together can form a heterocyclic ring having 5 to 7 ring atoms; Class 2 comprises macrocyclic compounds represented by formula IV ##STR30## wherein Z 2 is a diradical --O--, --S--, or --NH--; wherein each R 2 independently can be hydrogen or it can be R 1 as previously defined, or two R 2 s together can form at least one ring which is saturated or unsaturated and the ring can be substituted or unsubstituted with alkyl, alkenyl or alkynyl groups containing from 1 to 30 carbon atoms; the carbon atoms can be interrupted with up to 10 individual, non-catenated heteroatoms selected from O, S, and N; x is 1 or 2, and bis an integer from 3 to 10; Class 3 is represented by compounds having formulae V and VI, ##STR31## wherein each R 2 independently is as previously defined; and a class of tripyridyltriazines ##STR32## wherein each R 2 independently is as previously defined; Class 4 is described by compounds of formula VII: ##STR33## where Z 3 is nitrogen, phosphorus, arsenic or antimony; where each R 1 independently is as defined above, and R 3 can be R 1 or a difunctional group selected from alkylene and phenylene groups, wherein c is either 1 or 2; Class 5 describes Schiff bases and can be represented by compounds of formula VIII: ##STR34## wherein R 2 and R 3 independently are as previously defined, and wherein d is 1 or 2.
Claim 3
Dependent Claim
15 words
The composition according to claim 1 further comprising at least one mono or poly alcohol.
Claim 4
Dependent Claim
18 words
The composition according to claim 1 further comprising at least one additive to increase the speed of cure.
Claim 5
Dependent Claim
17 words
The composition according to claim 1 wherein said cationically curable monomer is at least one epoxy monomer.
Claim 6
Dependent Claim
18 words
The composition according to claim 1 wherein said cationically curable monomer is at least one vinyl ether-containing monomer.
Claim 7
Dependent Claim
207 words
The composition according to claim 1 wherein said salt of an organometallic complex cation has the formula [(L.sup.1).sub.y (L.sup.2).sub.z M].sup.+q X.sub.n (I) wherein M is selected from the group containing Cr, Ni, Mo, W, Mn, Tc, Re, Fe, Ru, Os, Co, Rh and Ir; L 1 represents none, one or two of the same or different ligands contributing pi-electrons that can be selected from aromatic compounds and heterocyclic aromatic compounds, and capable of contributing six pi-electrons to the valence shell of M; L 2 represents none, one or two of the same or different ligands contributing pi-electrons that can be selected from cyclopentadienyl and indenyl anion groups, and capable of contributing six pi-electrons to the valence shell of M; q is an integer having a value of 1 or 2, the residual charge of the complex cation; y and z are integers having a value of zero, one, or two, provided that the sum of y and z is equal to 2; X is an anion selected from organic sulfonate anions and halogen-containing complex anions of a metal or metalloid; and n is an integer having a value of 1 or 2, the number of complex anions required to neutralize the charge q on the complex cation.
Claim 8
Dependent Claim
28 words
The composition according to claim 1 wherein said salt is selected from the group consisting of bis-(eta 6 -arene) iron complex cations and bis(eta 5 -cyclopentadienyl)iron complex cations.
Claim 9
Dependent Claim
30 words
The composition according to claim 1 wherein said stabilizing additive used with bis-(eta 6 -arene)iron complex cations has a formula selected from the group consisting of classes 1 to 3.
Claim 10
Dependent Claim
29 words
The composition according to claim 1 wherein said stabilizing additive used with bis-(eta 5 -cyclopentadienyl)iron complex cations is selected from the group consisting of classes 2, 4, and 5.
Claim 11
Dependent Claim
15 words
The composition according to claim 1 wherein said stabilizing additive is said class 1 compound.
Claim 12
Dependent Claim
15 words
The composition according to claim 1 wherein said stabilizing additive is said class 2 compound.
Claim 13
Dependent Claim
15 words
The composition according to claim 1 wherein said stabilizing additive is said class 3 compound.
Claim 14
Dependent Claim
15 words
The composition according to claim 1 wherein said stabilizing additive is said class 4 compound.
Claim 15
Dependent Claim
15 words
The composition according to claim 1 wherein said stabilizing additive is said class 5 compound.
Claim 16
Dependent Claim
7 words
The cured composition according to claim 1.
Claim 17
Dependent Claim
7 words
The cured composition according to claim 2.
Claim 18
Dependent Claim
7 words
The cured composition according to claim 3.
Claim 19
Dependent Claim
42 words
A process comprising the steps: a) providing the curable composition according to claim 1, and b) adding sufficient energy to the composition in the form of at least one of heat and light in any combination and order to cure said composition.
Claim 20
Dependent Claim
25 words
An article having on at least one surface thereof a layer of the composition according to claim 1, said composition optionally further comprising abrasive particles.
Claim 21
Dependent Claim
15 words
The article according to claim 19 wherein said layer of the composition is an adhesive.
Claim 22
Dependent Claim
21 words
An article comprising a substrate having on at least one surface thereof a layer of the composition according to claim 15.
Claim 23
Dependent Claim
16 words
The article according to claim 21 wherein said layer of the compound is a protective coating.
Claim 24
Dependent Claim
21 words
An article comprising a substrate having on at least one surface thereof a layer of the composition according to claim 16.
Claim 25
Dependent Claim
21 words
An article comprising a substrate having on at least one surface thereof a layer of the composition according to claim 17.
Claim 26
Dependent Claim
58 words
A process comprising the steps: a) coating at least one surface of a substrate with a layer of the energy polymerizable composition according to claim 1, and b) supplying sufficient energy to the composition in the form of at least one of heat and light in any combination and order for a time sufficient to cure said composition.
References Cited (Backward Citations)
US3816280A
Cited
GB1404242A
Cited
US5191101A
Cited
US5089536A
Cited
US5073476A
Cited
AU3855185A
Cited
US4503211A
Cited
CA1277070C
Cited
US4707432A
Cited
US4751138A
Cited
US4920182A
Cited
US4846905A
Cited
US4985340A
Cited
US5047376A
Cited
US5130406A
Cited
US5179179A
Cited
CA2040010A1
Cited
EP0511405A1
Cited
US5296567A
Cited
US5252694A
Cited
US5362421A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1999-02-26 | 1999-08-28 | 2000-02-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-02-26 | 2003-08-28 | 2004-02-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-02-26 | 2007-08-28 | 2008-02-27 | $7700.00 | Window Closed / Lapsed |