Cyanoacrylate adhesive composition

Claim 2

An alpha-cyanoacrylate composition containing as stabilizer a stabilizing amount of one or more sulfonic acid derivatives of the formula: ##STR10## in which R 1 stands for a trimethylsilyl group Si(CH 3 ) 3 , R 2 is a halogen atom, a straight or branched-chain alkyl group having 1 to 10 carbon atoms, a perfluoroalkyl group having 1 to 10 carbon atoms, a phenyl group or a tolyl group.

Claim 3

A composition according to claim 1 which additionally contains as a co-stabilizer one or more sulfonic acid derivatives of the formula: ##STR11## wherein R 3 is an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 7 carbon atoms or a nitro group and M has a value of 0, 1, 2 or 3.

Claim 4

A composition according to claim 1 which additionally contains as a co-stabilizer one or more sulfonic acid derivatives of the formula: ##STR12## wherein R 4 and R 5 can be the same or different and stand for hydrogen or alkyl radicals.

Claim 5

A composition according to claim 1 which additionally contains as a co-stabilizer one or more (dihydroxy)-organylborane or bis(dihydroxyboryl) derivatives of the formula: R.sup.6 [B(OH).sub.2 ].sub.m (III) in which m is 1 or 2 and R 6 is a straight or branched-chain alkyl or alkylene group having 1 to 12 carbon atoms, which can be substituted by halogen atoms, or R 6 is a cyclohexyl or cyclohexylene group, an aralkyl or aralkylene group containing from 7 to 9 carbon atoms or a phenyl or phenylene group.

Claim 6

A composition according to claim 2 which additionally contains as a co-stabilizer one or more (dihydroxy)-organylborane or bis(dihydroxyboryl) derivatives of the formula: R.sup.6 [B(OH).sub.2 ].sub.m (III) in which m is 1 or 2 and R 6 is a straight or branched-chain alkyl or alkylene group having 1 to 12 carbon atoms, which can be substituted by halogen atoms, or R 6 is a cyclohexyl or cyclohexylene group, an aralkyl or aralkylene group containing from 7 to 9 carbon atoms or a phenyl or phenylene group.

Claim 7

A composition according to claim 3 which additionally contains as a co-stabilizer one or more (dihydroxy)-organylborane or bis(dihydroxyboryl) derivatives of the formula: R.sup.6 [B(OH).sub.2 ].sub.m (III) in which m is 1 or 2 and R 6 is a straight or branched-chain alkyl or alkylene group having 1 to 12 carbon atoms, which can be substituted by halogen atoms, or R 6 is a cyclohexyl or cyclohexylene group, an aralkyl or aralkylene group containing from 7 to 9 carbon atoms or a phenyl or phenylene group.

Claim 8

An alpha-cyanoacrylate composition comprising as stabilizer a stabilizing amount of one or more of the following compounds: (A) sulfonic acid derivatives of the formula: ##STR13## in which R 1 stands for a trimethylsilyl group Si(CH 3 ) 3 , R 2 is a halogen atom, a straight or branched-chain alkyl group having 1 to 10 carbon atoms, a perfluoroalkyl group having 1 to 10 carbon atoms, a phenyl group or a tolyl group or R 1 and R 2 together, accompanied by cyclization, stand for a group of the formula: ##STR14## in which Z is bonded directly to sulfur and is an aromatic radical of the formula: ##STR15## wherein R 3 is an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 7 carbon atoms or a nitro group and m has a value of 0, 1, 2, or 3, or Z is an aliphatic radical of the formula --CR 2 4 --CR 2 5 -- wherein R 4 and R 5 can be the same or different and stand for hydrogen or alkyl radicals; and one or more of the following compounds: (B) (dihydroxy)-organylboranes and bis(dihydroxyboryl)-derivatives of the formula: R.sup.6 [B(OH).sub.2 ].sub.m (III) in which m is 1 to 2, R 6 is a straight or branched-chain alkyl or alkylene group having 1 to 12 carbon atoms, which can be substituted by halogen atoms, or R 6 is a cyclohexyl or cyclohexylene group, an aralkyl or aralkylene group containing from 7 to 9 carbon atoms or a phenyl or phenylene group.

Claim 9

An alpha-cyanoacrylate composition comprising as stabilizer a stabilizing amount of one or more of the following compounds: (A) sulfonic acid derivatives of the formula: ##STR13## in which R 1 stands for a trimethylsilyl group Si(CH 3 ) 3 , R 2 is a halogen atom, a straight or branched-chain alkyl group having 1 to 10 carbon atoms, a perfluoroalkyl group having 1 to 10 carbon atoms, a phenyl group or a tolyl group or R 1 and R 2 together, accompanied by cyclization, stand for a group of the formula: ##STR14## in which Z is bonded directly to sulfur and is an aromatic radical of the formula: ##STR15## wherein R 3 is an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 7 carbon atoms or a nitro group and m has a value of 0, 1, 2, or 3, or Z is an aliphatic radical of the formula --CR 2 4 --CR 2 5 -- wherein R 4 and R 5 can be the same or different and stand for hydrogen or alkyl radicals; and one or more of the following compounds: (B) (dihydroxy)-organylboranes and bis(dihydroxyboryl)-derivatives of the formula: R.sup.6 [B(OH).sub.2 ].sub.m (III) in which m is 1 to 2, R 6 is a straight or branched-chain alkyl or alkylene group having 1 to 12 carbon atoms, which can be substituted by halogen atoms, or R 6 is a cyclohexyl or cyclohexylene group, an aralkyl or aralkylene group containing from 7 to 9 carbon atoms or a phenyl or phenylene group.

Claim 10

A composition according to claim 7 comprising as stabilizer (i) a (dihydroxy)-organylborane or bis(dihydroxyboryl) derivatives of the formula III; and (ii) as sulfonic acid derivative having the group of the formula II wherein Z in the aliphatic radical designated in claim 7.

Claim 11

A composition according to claim 7 comprising as stabilizer (i) a (dihydroxy)-organylborane or bis(dihydroxyboryl) derivative of the formula III; and (ii) a sulfonic acid derivative having the group of the formula II wherein Z is the aromatic radical designated in claim 7.