US5147900A — Energy-induced dual curable compositions

Claim 1

Independent Claim 262 words

An energy polymerizable composition comprising a) least one ethylenically-unsaturated monomer b) at least one epoxy monomer different from the monomer in a) c) a curing agent comprising (1) an organometallic compound, and (2) an onium salt, wherein said organometallic compound has 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 metal atoms selected from the elements of Periodic Groups IVB, VB, VIB, VIIB, and VIII; 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 262 words

An energy polymerizable composition comprising a) least one ethylenically-unsaturated monomer b) at least one epoxy monomer different from the monomer in a) c) a curing agent comprising (1) an organometallic compound, and (2) an onium salt, wherein said organometallic compound has 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 metal atoms selected from the elements of Periodic Groups IVB, VB, VIB, VIIB, and VIII; 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 38 words

The composition according to claim 1 wherein said onium salt has the formula II AX II wherein A is an iodonium on sulfonium cation, 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 epoxy compound 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, acrylamides 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 13 words

The composition according to claim 1 wherein said epoxy compound is a 1,2-epoxide.

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 92 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 19 words

A layered structure comprising a substrate having coated on one surface thereof the polymerizable composition according to claim 2.

Claim 16

Dependent Claim 7 words

The cured structure according to claim 14.

Claim 17

Dependent Claim 12 words

The layered structure according to claim 14 which is an imageable structure.

Claim 18

Dependent Claim 258 words

An energy polymerizable composition comprising a) at least one ethylenically-unsaturated monomer b) at least one epoxy monomer different from the monomer in a) c) a curing agent comprising (1) an organometallic compound, and (2) an onium salt, wherein said organometallic compound has 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 metal atoms selected from the elements of Periodic Group VIII; 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 19

Dependent Claim 258 words

An energy polymerizable composition comprising a) at least one ethylenically-unsaturated monomer b) at least one epoxy monomer different from the monomer in a) c) a curing agent comprising (1) an organometallic compound, and (2) an onium salt, wherein said organometallic compound has 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 metal atoms selected from the elements of Periodic Group VIII; 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 20

Dependent Claim 282 words

A process comprising the steps of: a) providing a polymerizable mixture comprising (1) at least one ethylenically-unsaturated compound, and (2) at least one epoxy monomer, and (3) a catalytically effective amount of a curing agent comprising (a) an 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 metal atoms selected from the elements of Periodic Groups IVB, VB, VIB, VIIB, and VIII; 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; and (b) an onium salt; b) allowing said mixture to polymerize or adding energy to said mixture to effect polymerization.

Claim 21

Dependent Claim 282 words

A process comprising the steps of: a) providing a polymerizable mixture comprising (1) at least one ethylenically-unsaturated compound, and (2) at least one epoxy monomer, and (3) a catalytically effective amount of a curing agent comprising (a) an 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 metal atoms selected from the elements of Periodic Groups IVB, VB, VIB, VIIB, and VIII; 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; and (b) an onium salt; b) allowing said mixture to polymerize or adding energy to said mixture to effect polymerization.

Claim 22

Dependent Claim 21 words

The method according to claim 18 wherein said energy is at least one of electromagnetic radiation, accelerated particles, or thermal energy.

Claim 23

Dependent Claim 25 words

The method according to claim 18 wherein said polymerizable mixture further comprises up to 90 weight percent of a solvent based on the total mixture.

Claim 24

Dependent Claim 11 words

A cured composition prepared according to the method of claim 18.

Claim 25

Dependent Claim 7 words

A shaped article according to claim 21.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1995-09-15	1996-03-16	1996-09-15	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1999-09-15	2000-03-16	2000-09-15	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2003-09-15	2004-03-16	2004-09-15	$7700.00	Window Closed / Lapsed

Energy-induced dual curable compositions

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