US5453450A — Stabilized curable adhesives

Claim 1

Independent Claim 290 words

A stablized heat curable adhesive prepared from a formulation comprising: (1) at least one free radically polymerizable monomer; (2) at least one epoxy function monomer; (3) at least one free radical polymerization photoinitiator; (4) a thermally-initiated cationic catalyst system comprising: (a) at least one salt of an organometallic cation, wherein the salt of the organometallic cation is selected from the class of substituted and unsubstituted aromatic compounds based on a benzene or cyclopentadienyl nucleus, the metal atom is a transition metal atom, and the anion is tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, or hexafluoroantimonate; b) at least one stabilizing additive, wherein the stabilizing additive has a segment or central nucleus of a formula selected from the group consisting of ##STR6## wherein R 1 is a radical moiety that can be the same or different and is selected from substituted and unsubstituted C 1 to C 10 alkyl groups, substituted and unsubstituted groups of one to four aromatic rings, wherein two to four rings can be fused or unfused rings; R 2 is hydrogen or R 1 further when R 2 is R 1 , R 1 and R 2 taken together can form a cyclic ring having 5 to 7 ring atoms; R 3 is R 1 or divalent group (as when d=2) selected from alkylene, having 3 to 10 carbon atoms and phenylene groups; R 4 is hydrogen, and each R 3 may be independently selected and is as defined above, and further two adjacent R 3 groups may be taken together to form a cyclic ring having 5 to 7 ring atoms; Z is nitrogen, phosphorus, arsenic or antimony; c is 1 or 2; and d is 1 or 2; (5) optionally, at least on alcohol-containing material; and (6) optionally, adjuvants.

Claim 2

Dependent Claim 290 words

A stablized heat curable adhesive prepared from a formulation comprising: (1) at least one free radically polymerizable monomer; (2) at least one epoxy function monomer; (3) at least one free radical polymerization photoinitiator; (4) a thermally-initiated cationic catalyst system comprising: (a) at least one salt of an organometallic cation, wherein the salt of the organometallic cation is selected from the class of substituted and unsubstituted aromatic compounds based on a benzene or cyclopentadienyl nucleus, the metal atom is a transition metal atom, and the anion is tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, or hexafluoroantimonate; b) at least one stabilizing additive, wherein the stabilizing additive has a segment or central nucleus of a formula selected from the group consisting of ##STR6## wherein R 1 is a radical moiety that can be the same or different and is selected from substituted and unsubstituted C 1 to C 10 alkyl groups, substituted and unsubstituted groups of one to four aromatic rings, wherein two to four rings can be fused or unfused rings; R 2 is hydrogen or R 1 further when R 2 is R 1 , R 1 and R 2 taken together can form a cyclic ring having 5 to 7 ring atoms; R 3 is R 1 or divalent group (as when d=2) selected from alkylene, having 3 to 10 carbon atoms and phenylene groups; R 4 is hydrogen, and each R 3 may be independently selected and is as defined above, and further two adjacent R 3 groups may be taken together to form a cyclic ring having 5 to 7 ring atoms; Z is nitrogen, phosphorus, arsenic or antimony; c is 1 or 2; and d is 1 or 2; (5) optionally, at least on alcohol-containing material; and (6) optionally, adjuvants.

Claim 3

Dependent Claim 20 words

The stabilized heat curable adhesive according to claim 1 wherein the free radically polymerizable monomers are acrylate or methacrylate materials.

Claim 4

Dependent Claim 300 words

The stabilized heat curable ahdesive according to claim 1 wherein the salt of an organometallic cation has the formula: [(L.sup.1).sub.m (L.sup.2).sub.p ].sup.+q X.sub.n wherein: M is selected from the group containing Cr, Mo, W, Mn, Re, Fe, Ru, and Os; L 1 represents ligands contributing π-electrons that can be selected from substituted and unsubstituted aromatic compounds and substituted and unsubstituted heterocyclic aromatic compounds, and capable of contributing six π-electrons to the valence shell of M; L 2 represents ligands contributing π-electrons that can be selected from substituted and unsubstituted cyclopentadienyl and indenyl anions, and capable of contributing six π-electrons to the valence shell of M; m and p are integers having a value of 0 or 2, such that, when m is equal to 2, each L 1 may be the same or different ligands and p is equal to 0; and when p is equal to 2, each L 2 may be the same or different ligands and m is equal to 0, provided the sum of (m+p) is equal to 2; q is an integer having a value of 1 or 2, the residual charge of the complex cation; X is an anion selected from organic sulfonate anions selected from the group consisting of CH 3 SO 3 - , CF 3 SO 3 - , C 6 H 5 SO 3 - , p-toluenesulfonate, p-chlorobenzenesulfonate and related isomers, and halogen-containing complex anions of a metal or metalloid selected from the group consisting of BF 4 - , AsF 6 - , PF 6 - , SbF 5 OH - , SbF 6 - , CF 3 SO 3 - ; 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 5

Dependent Claim 76 words

A stabilized heat curable adhesive comprising: (1) at least one free radically polymerizable monomer selected from the group consisting of n-butyl acrylate, isobornyl acrylate, tetrahydrofurfuryl acrylate, and phenoxyethyl acrylate; (2) at least one diglycidyl ether of bisphenol A monomers; (3) 2,2-dimethoxy-2-phenylacetophenone; (4) a thermally-initiated cationic catalyst system comprising: (a) either bis(η 5 -cyclopentadienyl)iron(1+) hexafluoroantimonate or bis(η 6 -mesitylene)iron(2+) hexafluoroantimonate; and (b) either 1,10-phenanthroline or ##STR7## (5) optionally, at least one alcohol-containing material; and (6) optionally, adjuvants.

Claim 6

Dependent Claim 76 words

A stabilized heat curable adhesive comprising: (1) at least one free radically polymerizable monomer selected from the group consisting of n-butyl acrylate, isobornyl acrylate, tetrahydrofurfuryl acrylate, and phenoxyethyl acrylate; (2) at least one diglycidyl ether of bisphenol A monomers; (3) 2,2-dimethoxy-2-phenylacetophenone; (4) a thermally-initiated cationic catalyst system comprising: (a) either bis(η 5 -cyclopentadienyl)iron(1+) hexafluoroantimonate or bis(η 6 -mesitylene)iron(2+) hexafluoroantimonate; and (b) either 1,10-phenanthroline or ##STR7## (5) optionally, at least one alcohol-containing material; and (6) optionally, adjuvants.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1998-09-25	1999-03-27	1999-09-26	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2002-09-25	2003-03-27	2003-09-26	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2006-09-25	2007-03-27	2007-09-26	$7700.00	Window Closed / Lapsed

Stabilized curable adhesives

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