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AssigneeLoctite (R&D) Limited
InventorsBernard Ryan, Hanns Roland Misiak, James A Houlihan, Gerard R MacCann
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An activator composition for the accelerated hardening of cyanoacrylate adhesives, wherein the activator comprises a member selected from the group consisting of: aromatic heterocyclic compounds having at least one N hetero atom in the ring(s) such as pyridines, quinolines and pyrimidines and substituted on the ring(s) with at least one electron-withdrawing group which decreases the base strength of the substituted compound compared to the corresponding unsubstituted compound, mixtures of any of the foregoing with each other, and/or with N,N-dimethyl-p-toluidine, and mixtures of any of the foregoing and/or N,N-dimethyl-p-toluidine with an organic compound containing the structural element, —N═C—S—S—, such as dibenzothiazyl disulfide. 6,6′dithiodinicotinic acid, 2,2′dipyridyl disulfide, and bis(4-t-butyl-1-isopropyl-2-imidazolyl) disulfide. An activator composition may comprise a solution of one or more activators in a solvent mixture which comprises a volatile hydrocarbon and a cyclic ketone.
An activator composition for the accelerated hardening of cyanoacrylate adhesives, wherein the activator comprises a mixture of:
A composition according to any of claims 1-6 wherein the activator comprises a member (A) selected from the group consisting of pyridines, quinolines and pyrimidines substituted with at least one electron-withdrawing group which decreases the base strength of the substituted compound compared to the corresponding unsubstituted compound.
An activator composition for the accelerated hardening of a cyanoacrylate adhesives throughout the adhesive, wherein the activator comprises a member selected from the group consisting of:
An activator composition for the accelerated hardening of cyanoacrylate adhesives, wherein the activator comprises a mixture of a 3,5-dihalopyridine and an organic compound having the structural element, —N═C—S—S—.
A composition comprising a mixture of a 3,5-dihalopyridine and an organic compound having the structural element, —N═C—S—S—.
An activator composition for the accelerated hardening of cyanoacrylate adhesives, wherein the activator comprises a member selected from the group consisting of:
A composition comprising a mixture of:
Use of a composition according to at least one of the preceding claims for the accelerated hardening of a cyanoacrylate adhesive.
An activator composition for the accelerated hardening of cyanoacrylate adhesives, wherein the composition comprises a solution of one or more activators in a solvent mixture which comprises a volatile hydrocarbon and a cyclic ketone.
42 A composition according to claim 41 wherein the cyclic ketone is present in an amount of at least about 3% by weight of the solvent mixture.
Dependencies are inferred from the claim text.
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This invention relates to activator compositions, particularly well suited for accelerating the hardening of cyanoacrylate adhesives. The invention also relates to novel mixtures of chemical compounds and to the use of the activator compositions and the novel mixtures for the accelerated hardening of cyanoacrylate adhesives. The invention further relates to a process for the accelerated bonding of substrates using cyanoacrylate adhesives.
Adhesive compositions based upon cyanoacrylate esters are well known and have found extensive use, because of their rapid cure speed, excellent long-term bond strength, and applicability to a wide variety of substrates. They generally harden after only a few seconds, after which the joined parts exhibit at least a certain degree of initial strength.
It is known that certain cyanoacrylate (CA) adhesives typically harden by an anionic polymerisation reaction. If the adhesive is conventionally applied in a relatively thick layer in the joint gap or relatively large amounts of adhesive are applied so that relatively large drops of adhesive protrude from between the parts to be joined, rapid hardening throughout the adhesive may rarely be achieved, i.e. cure-through-gap or cure-through-volume (CTV) performance may be unsatisfactory.
In the Examples, the following abbreviations and terms are used: 1 DCP = 3,5-dichloro pyridine, DBP = 3,5-dibromo pyridine, NQ = 5-nitro quinoline DCQ = 4,7-dichloro quinoline, DPDS = 2,2′-dipyridyl disulfide, BBID = Bis(4-t-butyl-isopropyl-2-imidazolyl) disulfide, DMPT = N,N-dimethyl-p-toluidine, NBP = n-bromopropane, Heptane = n-heptane, CTV = cure through volume CNP = 3-Cyano Pyridine THF = tetrahydrofuran <1% CNP = Saturated solution of CNP in heptane, it was not fully soluble at 1% concentration BP = 5-bromo pyrimidine, ACP - 2-acetyl pyridine DPPDC = Dipropyl 3,5-Pyridine Dicarboxylate, BNA = 5-bromo nicotinic acid in IPA solvent MPyr = 2-methoxy pyrazine; MTPyr = 2-methylthio pyrazine IPA = isopropyl alcohol solvent, DIOX = 1,4-dioxane solvent HPOL = heptan-1-ol solvent, DCB = 1,2-dichloro benzene solvent s = seconds MS = mild steel Loctite 401, Loctite 411, Black Max/Loctite 380, Loctite 416 and Loctite 424 = Different grades of Loctite ethyl cyanoacrylate-based adhesive 7457 = Loctite 7457 (activator) 7455 = Loctite 7455 (activator).
Loctite 401 (also called 401 herein) is a low viscosity, fast curing, single component ethyl cyanoacrylate adhesive (see for example U.S. Pat. No. 4,695,615).
Loctite 411 (also called 411 herein) is a single component high viscosity ethyl cyanoacrylate adhesive formulated for impact and peel resistance (see for example U.S. Pat. No. 4,477,607)