US 11,299,651 B2 · Toughened cyanoacrylate compositions

Abstract

Curable cyanoacrylate compositions are reported that comprise cyanoacrylate and a thermoplastic polyurethane (TPU) components. Such compositions are toughened cyanoacrylate compositions exhibiting long term viscosity stability when stored for prolonged periods at room temperature (25° C.). TPU components are reported having structural units in which at least one of the structural units has the formula —O—R1—O—Ar—O—R2—O—, wherein Ar is a C6-C20 aromatic group with at least one aromatic ring; R1 is a C2-C10 alkyl group; and R2 is a C2-C10 alkyl group. The thermoplastic polyurethane (TPU) component may be present in the curable cyanoacrylate composition from about 1 wt % to about 40 wt %, for example from about 2 wt % to about 30 wt %, such from about 3 wt % to about 20 wt %, suitably from about 5 wt % to about 10 wt %, based on the total weight of the composition.

Claims24

Dependent claims

A curable cyanoacrylate composition comprising:

(i) a cyanoacrylate;
and
(ii) a thermoplastic polyurethane (TPU) having a chain formed from structural units;
wherein at least one of the structural units of the chain of the TPU (ii) has the formula:
—O—R1—O—Ar—O—R2—O—,
wherein:
Ar is a C6-C20 aromatic group with at least one aromatic ring;
R1 is a C2-C10 alkyl group;
and
R2 is a C2-C10 alkyl group,
and wherein the TPU (ii) is present in the curable cyanoacrylate composition from about 1 wt % to about 40 wt %, based on the total weight of the composition.

8 more elements

A method of preparing a curable cyanoacrylate composition that retains a stable viscosity for at least 30 days when stored at 25° C., the viscosity measured at 25° C., wherein the method involves preparing a composition comprising from about 60 wt % to about 90 wt % of a cyanoacrylate with from about 1 wt % to about 40 wt % of a TPU, wherein the percentages are by weight based on the total weight of the composition and wherein the TPU has been prepared from:

a polyol selected from the group consisting of a polyester-polyol, a co-polyester-polyol, a polyether-polyol, a co-polyether-polyol, a polycaprolactone-polyol, and a co-polycaprolactone-polyol;
and
an isocyanate compound selected from the group consisting of 1,4-diisocyanatobenzene (PPDI), toluene diisocyanate (TDI), 4,4′-diphenylmethane diisocyanate (4,4′-MDI), 2,4′-diphenylmethane diisocyanate (2,4′-MDI), polymethylene poly(phenyl isocyanate) (PMDI), 1,5-naphthalene diisocyanate (NDI), bitolylene diisocyanate (TODI), 1,3-xylene diisocyanate (XDI),p-1,1,4,4-tetramethylxylene diisocyanate (p-TMXI), m-1,1,3,3-tetramethylxylylene diisocyanate (m-TMXDI), 1,6-diisocyanato-2,4,4-trimethylhexane, 1,4-cyclohexane diisocyanate (CHDI), 1,4-cyclohexanebis(methylene isocyanate) (BDI), 1,3-bis(isocyanatomethyl)cyclohexane (H6XDI), 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate (IPDI), dicyclohexylmethane diisocyanate (H12MDI), and triphenylmethane -4,4′,4″-triisocyanate;
and
a chain extender with the formula:
HO—R1—O—Ar—O—R2—OH,
wherein Ar is a C6-C20 aromatic group with at least one ring,
R1 is a C2-C10 alkyl group, and
R2 is a C2-C10 alkyl group.

6 more elements

Dependencies are inferred from the claim text.

Toughened cyanoacrylate compositions

Life of this patent

Toughened cyanoacrylate compositions

Life of this patent

Abstract

Claims24