Anaerobic adhesive compositions

Claim 2

An anaerobic curing adhesive composition comprising in combination (a) a first part comprising free radical polymerizable acrylic or substituted acrylic monomer(s) and diaryl iodonium salt in an amount sufficient to initiate polymerization of said monomer(s), and in contact therewith (b) a second part activator comprising an aldehyde-amine condensation product, wherein the acrylic or substituted acrylic monomer of the first part is a member of the group consisting of compounds of the formula: ##STR10## wherein R is selected from the group consisting of hydrogen methyl, ethyl, ##STR11## R' is selected from the group consisting of hydrogen, chlorine, methyl, and ethyl, R" is selected from the group consisting of hydrogen, hydroxy, and ##STR12## m is an integer from 1 to 8, n is an integer from 1 to 20, and p is 0 or 1; ##STR13## wherein R represents hydrogen, chlorine, methyl or ethyl, R' represents alkylene with 2-6 carbon atoms, R' represents (CH 2 ) m in which m is an integer of from 0 to 8, ##STR14## n represents an integer of from 1 to 4; ##STR15## wherein X is selected from the group consisting of ##STR16## and R is a member selected from the group consisting of hydrogen and lower alkyl of 1 to 7 carbon atoms; A represents the organic residue of an active hydrogen containing acrylic ester wherein the active hydrogen has been removed, the ester being hydroxy or amino substituted on the alkyl portion thereof and the methyl, ethyl and chlorine homologs thereof; n is an integer from 1 to 6 inclusive; and B is a mono- or polyvalent organic radical selected from the group consisting of alkyl, alkylene, alkenyl, cycloalkyl, cycloalkylene, aryl, aralkyl, alkaryl, poly(oxyalkylene), poly (carboalkoxyalkylene), and heterocyclic radicals both substituted and unsubstituted; ##STR17## where R 1 is methyl, ethyl, carboxyl or hydrogen; R 2 is hydrogen, methyl or ethyl; R 3 is hydrogen, methyl or hydroxyl; R 4 is hydrogen, chlorine, methyl or ethyl and n is an integer of from 0 to 8; and (e) monofunctional acrylate and methacrylate esters and the hydroxy, amide, cyano, chloro, and silane substituted derivatives thereof.

Claim 3

The adhesive composition of claim 1 wherein the diaryl iodonium salt is a salt of the formula ##STR18## wherein R 1 and R 2 are hydrogen, C 1 -C 12 alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, chloro, fluoro, bromo, iodo, carboxy and nitro groups; and X - is F - , Cl - , Br - , I - , NO 3 - , HSO 4 - , H 2 PO 4 - , HCOO - , CH 3 COO - , BF 4 - , AsF 6 - , PF 6 - , and SbF 6 - .

Claim 4

The adhesive composition of claim 1 wherein the diaryl iodonium salt is present in an amount from about 0.1 to 10% based on the weight of the monomer(s).

Claim 5

The adhesive composition of claim 1 wherein the acrylic or substituted acrylic monomer comprises hydroxyethyl methacrylate.

Claim 6

The adhesive composition of claim 1 wherein the acrylic or substituted acrylic monomer further comprises a polyurethane oligomer.

Claim 7

The adhesive composition of claim 1 wherein the acrylic or substituted acrylic monomer comprises poly(butylene maleate) dimethacrylate or poly(propylene glycol) dimethacrylate.

Claim 8

The adhesive composition of claim 1 wherein the activator comprises the reaction product of butyraldehyde and butylamine or butyraldehyde and aniline.

Claim 9

The adhesive composition of claim 1 wherein the diaryl iodonium salt is diphenyl iodonium chloride.

Claim 10

The adhesive composition of claim 1 wherein the diaryl iodonium salt is diphenyl iodonium 2-carboxylate.

Claim 11

The adhesive composition of claim 1 wherein the diaryl iodonium salt is diphenyl iodonium fluoroborate.

Claim 12

The adhesive composition of claim 1 wherein the diaryl iodonium salt is diphenyl iodonium hexafluorophosphate.

Claim 13

The adhesive composition of claim 1 wherein the diaryl iodonium salt is 3,3'dimethyldiphenyl iodonium hexafluorophosphate.

Claim 14

An article bonded with an adhesive composition comprising in combination (a) a first part comprising free radical polymerizable acrylic or substituted acrylic monomer(s) and diaryl iodonium salt in an amount sufficient to initiate polymerization of said monomer(s), and in contact therewith (b) a second part activator comprising an aldehyde-amine condensation product, wherein the diaryl iodonium salt corresponds to the formula ##STR19## wherein R 1 and R 2 are hydrogen, C 1 -C 12 alkyl, alkenyl, cycloakyl, cycloalkenyl, aryl, chloro, fluoro, bromo, iodo, carboxy and nitro groups; and X - is F - , Cl - , Br - , I - , NO 3 - , HSO 4 - , H 2 PO 4 - , HCOO - , CH 3 COO - , BF 4 - , AsF 6 - , PF 6 - , and SbF 6 - , and wherein the acrylic or substituted acrylic monomer of the first part is a member of the group consisting of compounds of the formula: ##STR20## wherein R is selected from the group consisting of hydrogen methyl, ethyl, ##STR21## R' is selected from the group consisting of hydrogen, chlorine, methyl and ethyl, R is selected from the group consisting of hydrogen, hydroxy, and ##STR22## m is an integer from 1 to 8, n is an integer from 1 to 20, and p is 0 or 1; ##STR23## wherein R represents hydrogen, chlorine, methyl or ethyl, R' represents alkylene with 2-6 carbon atoms, R" represents (CH 2 ) m in which m is an integer from 0 to 8, ##STR24## n represents an integer of from 1 to 4; ##STR25## wherein X is selected from the group consisting of ##STR26## and R is a member selected from the group consisting of hydrogen and lower alkyl of 1 to 7 carbon atoms; A represents the organic residue of an active hydrogen containing acrylic ester wherein the active hydrogen has been removed, the ester being hydroxy or amino substituted on the alkyl portion thereof and the methyl, ethyl and chlorine homologs thereof; n is an integer from 1 to 6 inclusive; and B is a mono- or polyvalent organic radical selected from the group consisting of alkyl, alkylene, alkenyl, cycloalkyl, cycloakylene, aryl, aralkyl, alkaryl, poly(oxyalkylene), poly(carboalkoxyalkylene), and heterocyclic radicals both substituted and unsubstituted; ##STR27## where R ` is methyl, ethyl, carboxyl or hydrogen; R 2 is hydrogen, methyl or ethyl; R 3 is hydrogen, methyl or hydroxyl; R 4 is hydrogen, chlorine, methyl or ethyl and n is an integer of from 0 to 8; and (e) monofunctional acrylate and methacrylate esters and the hydroxy, amide, cyano, chloro, and silane substituted derivatives thereof.

Claim 15

An article bonded with an adhesive composition comprising in combination (a) a first part comprising free radical polymerizable acrylic or substituted acrylic monomer(s) and diaryl iodonium salt in an amount sufficient to initiate polymerization of said monomer(s), and in contact therewith (b) a second part activator comprising an aldehyde-amine condensation product, wherein the diaryl iodonium salt corresponds to the formula ##STR19## wherein R 1 and R 2 are hydrogen, C 1 -C 12 alkyl, alkenyl, cycloakyl, cycloalkenyl, aryl, chloro, fluoro, bromo, iodo, carboxy and nitro groups; and X - is F - , Cl - , Br - , I - , NO 3 - , HSO 4 - , H 2 PO 4 - , HCOO - , CH 3 COO - , BF 4 - , AsF 6 - , PF 6 - , and SbF 6 - , and wherein the acrylic or substituted acrylic monomer of the first part is a member of the group consisting of compounds of the formula: ##STR20## wherein R is selected from the group consisting of hydrogen methyl, ethyl, ##STR21## R' is selected from the group consisting of hydrogen, chlorine, methyl and ethyl, R is selected from the group consisting of hydrogen, hydroxy, and ##STR22## m is an integer from 1 to 8, n is an integer from 1 to 20, and p is 0 or 1; ##STR23## wherein R represents hydrogen, chlorine, methyl or ethyl, R' represents alkylene with 2-6 carbon atoms, R" represents (CH 2 ) m in which m is an integer from 0 to 8, ##STR24## n represents an integer of from 1 to 4; ##STR25## wherein X is selected from the group consisting of ##STR26## and R is a member selected from the group consisting of hydrogen and lower alkyl of 1 to 7 carbon atoms; A represents the organic residue of an active hydrogen containing acrylic ester wherein the active hydrogen has been removed, the ester being hydroxy or amino substituted on the alkyl portion thereof and the methyl, ethyl and chlorine homologs thereof; n is an integer from 1 to 6 inclusive; and B is a mono- or polyvalent organic radical selected from the group consisting of alkyl, alkylene, alkenyl, cycloalkyl, cycloakylene, aryl, aralkyl, alkaryl, poly(oxyalkylene), poly(carboalkoxyalkylene), and heterocyclic radicals both substituted and unsubstituted; ##STR27## where R ` is methyl, ethyl, carboxyl or hydrogen; R 2 is hydrogen, methyl or ethyl; R 3 is hydrogen, methyl or hydroxyl; R 4 is hydrogen, chlorine, methyl or ethyl and n is an integer of from 0 to 8; and (e) monofunctional acrylate and methacrylate esters and the hydroxy, amide, cyano, chloro, and silane substituted derivatives thereof.

Claim 16

The article of claim 13 wherein the acrylic or substituted acrylic monomer comprises hydroxyethyl methacrylate and further comprises a polyurethane oligomer.

Claim 17

The article of claim 13 wherein the diaryl iodonium salt is diphenyl iodonium chloride or diphenyl iodonium 2-carboxylate.