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US4979993A Expired / Lapsed US ⏱️ 0.0 years remaining

Trialkylammonium alkyl carboxylate primer for cyanoacrylate bonding of polymeric substrates

Assignee: Henkel Loctite Corp
•
Filing: 1989-03-27
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Granted: 1990-12-25
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Expires: 2009-03-27
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Abstract

Abstract The invention relates to a tertiary ammonium alkyl carboxylate primer for bonding surfaces with cyanoacrylate adhesives, and to a method of bonding low surface energy surfaces using such tertiary ammonium alkyl carboxylates. A preferred primer is tridodecylammonium stearate and preferred solvents for the tertiary ammonium alkyl carboxylate are nonaqueous, low surface tension organic solvents.

Inventors

  • 👤 Yoshihisa Okamoto
  • 👤 Philip T. Klemarczyk

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 03:56
CPC Classifications
C; C08; C08J; C08J5/00; C08J5/12; C08J5/124

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 117 words
A non-aqueous primer composition for bonding surfaces with cyanoacrylate adhesives, consisting essentially of: (a) at least one tertiary ammonium carboxylate compound of the formula: ##STR6## wherein: R 1 , R 2 , R 3 , and R 4 may each vary independently of the others and are each selected from the group consisting of alkyl, alkenyl, alkynyl, alkylaryl and aralkyl; R 4 is a long chain moiety having 6-20 carbon atoms in the chain; and at least one of the R 1 , R 2 , and R 3 groups is a long chain moiety having 6-20 carbon atoms in the chain; and (b) a non-aqueous, low surface tension organic solvent for the tertiary ammonium carboxylate compound.
Claim 2
Dependent Claim 117 words
A non-aqueous primer composition for bonding surfaces with cyanoacrylate adhesives, consisting essentially of: (a) at least one tertiary ammonium carboxylate compound of the formula: ##STR6## wherein: R 1 , R 2 , R 3 , and R 4 may each vary independently of the others and are each selected from the group consisting of alkyl, alkenyl, alkynyl, alkylaryl and aralkyl; R 4 is a long chain moiety having 6-20 carbon atoms in the chain; and at least one of the R 1 , R 2 , and R 3 groups is a long chain moiety having 6-20 carbon atoms in the chain; and (b) a non-aqueous, low surface tension organic solvent for the tertiary ammonium carboxylate compound.
Claim 3
Dependent Claim 20 words
A primer composition according to claim 1, wherein R 4 is selected from the group consisting of alkyl and alkenyl.
Claim 4
Dependent Claim 59 words
A primer composition according to claim 1, wherein each of the R 1 , R 2 and R 3 groups comprising long chain moieties has at least 16 carbon atoms in the chain and each of the other R 1 , R 2 and R 3 groups is a short chain alkyl group having less than 5 carbon atoms.
Claim 5
Dependent Claim 38 words
A primer composition according to claim 1, wherein each of R 1 , R 2 , R 3 , and R 4 is independently selected from the group consisting of alkyl groups having 6 to 20 carbon atoms.
Claim 6
Dependent Claim 21 words
A primer composition according to claim 1, wherein R 4 COO.sup.⊖ is selected from the group consisting of oleate and stearate.
Claim 7
Dependent Claim 24 words
A primer composition according to claim 1, wherein R 4 is a long chain moiety having 10 to 15 carbon atoms in the chain.
Claim 8
Dependent Claim 16 words
A primer composition according to claim 1, wherein the tertiary ammonium carboxylate compound comprises distearylmethylammonium stearate.
Claim 9
Dependent Claim 16 words
A primer composition according to claim 1, wherein the tertiary ammonium carboxylate compound comprises distearylmethylammonium oleate.
Claim 10
Dependent Claim 16 words
A primer composition according to claim 1, wherein the tertiary ammonium carboxylate compound comprises tridodecylammonium stearate.
Claim 11
Dependent Claim 32 words
A primer composition according to claim 1, wherein the tertiary ammonium carboxylate compound has a concentration of from about 0.05% to about 1.0% by weight, based on the volume of the solvent.
Claim 12
Dependent Claim 12 words
A primer composition according to claim 1, wherein the solvent comprises isopropanol.
Claim 13
Dependent Claim 12 words
A primer composition according to claim 1, wherein the solvent comprises trichlorofluoroethane.
Claim 14
Dependent Claim 144 words
A non-aqueous primer composition for bonding surfaces with cyanoacrylate adhesives, consisting essentially of: (a) at least one tertiary ammonium carboxylate compound selected from the group consisting of: distearylmethylammonium stearate, tridodecylammonium stearate, disterylmethylammonium oleate, tridodecylammonium oleate, tridodecylammonium palmitate, methyltrioctylammonium stearate, and tristearylammonium stearate; and (b) a non-aqueous, low surface tension organic solvent for the tertiary ammonium carboxylate compound; wherein the non-aqueous, low surface tension organic solvent and the relative proportions of the tertiary ammonium carboxylate compound and the non-aqueous, low surface tension organic solvent are selected such that initial lap shear strength determined by the method of ASTM D-4502 STM-650 on polypropylene substrates bonded with cyanoacrylate adhesive is at least 1,000 psi, and that lap strength determined by said method on polypropylene substrates after 20 hours of open time prior to cyanoacrylate bonding is at least 80 percent of the initial lap shear strength value.
Claim 15
Dependent Claim 144 words
A non-aqueous primer composition for bonding surfaces with cyanoacrylate adhesives, consisting essentially of: (a) at least one tertiary ammonium carboxylate compound selected from the group consisting of: distearylmethylammonium stearate, tridodecylammonium stearate, disterylmethylammonium oleate, tridodecylammonium oleate, tridodecylammonium palmitate, methyltrioctylammonium stearate, and tristearylammonium stearate; and (b) a non-aqueous, low surface tension organic solvent for the tertiary ammonium carboxylate compound; wherein the non-aqueous, low surface tension organic solvent and the relative proportions of the tertiary ammonium carboxylate compound and the non-aqueous, low surface tension organic solvent are selected such that initial lap shear strength determined by the method of ASTM D-4502 STM-650 on polypropylene substrates bonded with cyanoacrylate adhesive is at least 1,000 psi, and that lap strength determined by said method on polypropylene substrates after 20 hours of open time prior to cyanoacrylate bonding is at least 80 percent of the initial lap shear strength value.
Claim 16
Dependent Claim 31 words
A non-aqueous primer composition composition according to claim 13, wherein the tertiary ammonium carboxylate compound is selected from the group consisting of distearylmethylammonium stearate, distearylammonium oleate, tridodecylammonium stearate, and tridodecylammonium oleate.
Claim 17
Dependent Claim 25 words
A non-aqueous primer composition according to claim 13, wherein the solvent is selected from the group consisting of alcohols, halogenated hydrocarbon solvents, and mixtures thereof.

References Cited (Backward Citations)

US2897170A Cited
US3260637A Cited
US3326742A Cited
US3332816A Cited
US3822312A Cited
JPS5028536A Cited
US4200549A Cited
US4450265A Cited
US4460759A Cited
US4554098A Cited
US4496685A Cited
DE3601518A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
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