Energy-polymerization adhesive, coating, film and process for making the same
AssigneeMinnesota Mining and Manufacturing Company
InventorsPeggy S. Willett, Janis Robins, Kent S. Tarbutton, Michael A. Kropp
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Abstract
Polymerizable compositions having at least one cationically polymerizable monomer; an optional free radically polymerizable monomer; an energy-polymerizable catalyst system wherein the catalyst system comprises an organometallic complex salt; a thermally decomposable ester reaction product of a tertiary alkyl alcohol and an acid that forms a chelation complex with the metal ion of the organometallic complex salt; optionally, a peroxide. The polymerized compositions are useful as cured adhesive films, pressure sensitive adhesives, protective coatings, liquid adhesives, structural and semi-structural adhesives, and free standing films.
Claims12
A polymerizable epoxy-acrylate composition comprising:
- (1) at least one free radically polymerizable monomer;
- (2) at least one cationically polymerizable monomer;
- (3) a catalyst system comprising:
- (a) at least one organometallic complex salt,
- (b) a thermally decomposable ester reaction product of a tertiary alkyl alcohol and an acid that forms a chelation complex with the metal ion of the organometallic complex salt,
- (c) optionally, peroxide, and
- (d) optionally, at least one free radical initiator;
- (4) optionally, a buffer compound;
- and
- (5) optionally, a mono- or polyfunctional alcohol.
A polymerizable epoxy-acrylate composition comprising:
- (1) 1-99 wt % of at least one free radically polymerizable monomer, wherein the free radically polymerizable monomer is selected from the group consisting of (meth)acrylates, (meth)acrylamide, and vinyl compounds;
- (2) 1-99 wt % of at least one free cationically polymerizable monomer, wherein the cationically polymerizable monomer is selected from the group consisting of epoxies, cyclic ethers, vinyl ethers, siloxanes, N-vinyl compounds, alpha-olefins, lactams, and lactones;
- (3) 0.01-20 wt % of a catalyst system comprising:
- (a) 0.01-19.99 wt % of at least one organometallic complex salt, wherein the organometallic complex salt is selected from the group consisting of
- (eta.sup.6 -xylenes(mixed isomers))(eta.sup.5 -cyclopentadienyl) iron (1+) hexafluoroantimonate,
- (eta.sup.6 -xylenes(mixed isomers))(eta.sup.5 -cyclopentadienyl) iron (1+) hexafluorophosphate,
- (eta.sup.6 -m-xylene)(eta.sup.5 -cyclopentadienyl)iron(1+) tetrafluoroborate, (eta.sup.6 -o-xylene)(eta.sup.5 -cyclopentadienyl)iron(1+) hexafluoroantimonate,
- (eta.sup.6 -p-xylenes)(eta.sup.5 -cyclopentadienyl)iron(1+) triflate,
- (eta.sup.6 -toluene)(eta.sup.5 -cyclopentadienyl)iron(1+) hexafluoroantimonate,
- (eta.sup.6 -cumene)(eta.sup.5 -cyclopentadienyl)iron(1+) hexafluoroantimonate,
- (eta.sup.6 -p-xylene)(eta.sup.5 -cyclopentadienyl)iron(1+) hexafluoroantimonate,
- (eta.sup.6 -m-xylene)(eta.sup.5 -cyclopentadienyl)iron(1+) hexafluoroantimonate,
- (eta.sup.6 -hexamethylbenzene)(eta.sup.5 -cyclopentadienyl)iron(1+) hexafluoroantimonate,
- (eta.sup.6 -naphthalene)(eta.sup.5 -cyclopentadienyl)iron(1+) hexafluoroantimonate,
- (eta.sup.6 -pyrene)(eta.sup.5 -cyclopentadienyl)iron(1+) hexafluoroantimonate,
- (eta.sup.6 -chrysene)(eta.sup.5 -cyclopentadienyl)iron(1+) hexafluoroantimonate,
- (eta.sup.6 -mesitylene)(eta.sup.5 -cyclopentadienyl)iron(1+) hexafluoroantimonate,
- (eta.sup.6 -cumene)(eta.sup.5 -cyclopentadienyl)iron(1+) hexafluorophosphate,
- (eta.sup.6 -mesitylene)(eta.sup.5 -cyclopentadienyl)iron(1+) pentafluorohydroxyantimonate, and
- (eta.sup.6 -toluene)(eta.sup.5 -cyclopentadienyl)iron(1+) hexafluoroarsenate,
- (b) 0.01-19.99 wt % of a thermally decomposable ester reaction product of a tertiary alkyl alcohol and an acid that forms a chelation complex with the metal ion of the organometallic complex salt,
- (c) 0 to 20 wt % of a peroxide, and
- (d) 0 to 20 wt % of at least one free radical initiator;
- (4) 0 to 20 wt % of a buffer compound,
- (5) 0 to 50 wt % of a mono- or polyfunctional alcohol, and
- (6) 0 to 97 wt % of adjuvants or thermoplastic polymers.
An epoxy-acrylate semi-structural, thermosettable pressure sensitive adhesive comprising (a) a cationically polymerizable monomer selected from the group consisting of digylcidyl ether of bisphenol A (epoxy eq. wt of 185-192 g/eq.), and digylcidyl ether of bisphenol A (epoxy eq. wt. of 525-550 g/eq.), (b) an acrylate monomer selected from the group consisting of butyl acrylate, 1,6-hexanediol diacrylate, tetrahydrofurfuryl acrylate, isooctyl acrylate, and tetraethylene glycol diacrylate, (c) Cp(Cum)Fe.sup.+ PF.sub.6.sup.- or Cp(Xyl)Fe.sup.+ SbF.sub.6.sup.-, (d) an oxalate ester, (e) cyclohexanedimethanol, (f) benzil dimethoxy ketal, and (g) a peroxide.
Dependencies are inferred from the claim text.