US 5,423,735 AGranted

Orthopedic cast composed of an alkoxysilane terminated resin

AssigneeMinnesota Mining and Manufacturing Company

InventorsAndrew Callinan, Matthew T. Scholz

Life of this patent

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Abstract

The present invention provides a water-curable resin composition for use in an orthopedic cast composed of a water-reactive alkoxysilane terminated resin, having at least one hydrolyzable group per molecule. The resin composition has a viscosity of no greater than about 500 Pa-s under ambient conditions and conditions less than about 1 wt-% of a solvent, based on the total weight of the resin composition.

Claims25

Dependent claims

An orthopedic casting material comprising:

(a) a water-curable resin composition containing less than about 1 wt-% of a solvent, said resin having a viscosity of no greater than about 500 Pa-s under ambient conditions, said resin composition comprising:
(i) a water-reactive alkoxysilane terminated prepolymer having at least one hydrolyzable group per molecule;
and
(ii) an effective amount of a catalyst to catalyze the polymerization of said alkoxysilane terminated prepolymer upon contact with water;
and
(b) a porous flexible substrate coated with the water-curable resin composition, wherein said orthopedic casting material is sufficiently porous to enable water to permeate a roll of said casting material during water activation and cause said resin to cure, and wherein said orthopedic casting material is sufficiently porous to allow air and moisture vapor to move through the material after it has been cured, wherein the water-reactive prepolymer is a compound of the formula;
##STR6## wherein:
(a) Q is a polyol residue;
(b) W is --NH--C(O)--X(R.sup.2.sub.2-n-q)-- or --X(R.sup.2.sub.2-n-q)--C(O)--NH--;
(c) X is --N--, --O--, or --S--;
(d) Y is --NH--, --O--, --S--, carbamylthio (--S--C(O)--NH--), carbamate (--O--C(O)--NH--), or unsubstituted or N-substituted ureido (--N(C(O)--NH--)--);
(e) R.sup.1 is a substituted or unsubstituted divalent bridging C.sub.1 -C.sub.200 hydrocarbon group, optionally interrupted in the backbone by 1-50 nonperoxide --O--, --C(O)--, --S--, --SO.sub.2 --, --N(R.sup.6)--, amide (--C(O)--NH--), ureido (--NH--C(O)--NH--), carbamate (--O--C(O)--NH--), carbamylthio (--S--C(O)--NH--), unsubstituted or N-substituted allophonate (--NH--C(O)--N(C(O)--NH--), unsubstituted or N-substituted biuret (--NH--C(O)--N(C(O)--NH--)--), and N-substituted isocyanurate groups;
(f) R.sup.2 can be present or absent, and is selected from the group consisting of H and a substituted or unsubstituted C.sub.1 -C.sub.20 hydrocarbon group, optionally interrupted in the backbone by 1-10 nonperoxide --O--, --C(O)--, --S--, --SO.sub.2 --, or --N(R.sup.6), groups;
(g) R.sup.3 is a substituted or unsubstituted divalent bridging C.sub.1 -C.sub.20 hydrocarbon group, optionally interrupted in the backbone by 1-5 nonperoxide --O--, --C(O)--, --S--, --SO.sub.2 --, or
(h) R.sup.4 is a C.sub.1 -C.sub.6 hydrocarbon group or --N.dbd.C(R.sup.7).sub.2 ;
(i) each R.sup.5 and R.sup.7 is independently a C.sub.1 -C.sub.6 hydrocarbon group;
(j) R.sup.6 is a H or a C.sub.1 -C.sub.6 hydrocarbon group;
(k) n=1-2 and q=0-1, with the proviso that when X is N, n+q=1, and when X is S or O, n+q=2;
(l) m=2-3;
(m) z=1-3;
and
(n) u=the functionality of the polyol residue=0-6, with the proviso that when u=0 the water-reactive prepolymer is a compound of formula ##STR7## wherein R.sup.1, W, R.sup.3, R.sup.4, R.sup.5, m, n, and z are as defined above.

19 more elements

An orthopedic support material comprising:

(a) a water-curable resin composition comprising:
(i) a water-reactive prepolymer of the formula:
##STR8## wherein:
(A) Q is a polyol residue;
(B) W is --NH--C(O)--X(R.sup.2.sub.2-n-q)-- or --X(R.sup.2.sub.2-n-q)--C(O)--NH--;
(C) X is --N--, --O--, or --S--;
(D) Y is --NH--,--O--, --S--, carbamylthio (--S--C(O)--NH--), carbamate (--0--C(O)--NH--), or unsubstituted or N-substituted ureido (--N(C(O)--NH--)--);
R.sup.1 is a substituted or unsubstituted divalent bridging C.sub.1 -C.sub.200 hydrocarbon group, optionally interrupted in the backbone by 1-50 nonperoxide --O--, --C(O)--, --S--, --SO.sub.2 --, --N(R.sup.6)--, amide (--C(O)--NH--), ureido (--NH--C(O)--NH--), carbamate (--O--C(O)--NH--), carbamylthio (--S--C(O)--NH--), unsubstituted or N-substituted allophonate (--NH--C(O)--N(C(O)--O--)--), unsubstituted or N-substituted biuret (--NH--C(O)--N(C(O)--NH--)--), and N-substituted isocyanurate groups;
(F) R.sup.2 can be present or absent, and is selected from the group consisting of a H and a substituted or unsubstituted C.sub.1 -C.sub.20 hydrocarbon group, optionally interrupted in the backbone by 1-10 nonperoxide --0--, --C(O)--, --S--, --SO.sub.2 --, or --N(R.sup.6)-- groups;
(G) R.sup.3 is a substituted or unsubstituted divalent bridging C.sub.1 -C.sub.20 hydrocarbon group, optionally interrupted in the backbone by 1-5 nonperoxide --O--, --C(O)--, --S--, --SO.sub.2 --, or --N(R.sup.6)--groups;
(H) R.sup.4 is a C.sub.1 -C.sub.6 hydrocarbon group or --N.dbd.C(R.sup.7).sub.2 ;
(I) each R.sup.5 and R.sup.7 is independently a C.sub.1 -C.sub.6 hydrocarbon group;
(J) R.sup.6 is a H or a C.sub.1 -C.sub.6 hydrocarbon group;
(K) n=1-2 and q=0-1, with the proviso that when X is N, n+q=1, and when X is S or O, n+q=2;
(L) m=2-3;
(M) z=1-3;
and
(N) u=the functionality of the polyol residue=0-6, with the proviso that when u=0, the water-reactive prepolymer is of the formula ##STR9## wherein R.sup.1, W, R.sup.3, R.sup.4, R.sup.5, m, n, and z are as defined above;
and
(ii) an effective amount of a catalyst to catalyze the polymerization of said alkoxysilane terminated prepolymer upon contact with water;
and
(b) a flexible substrate coated with the water-curable resin composition.

19 more elements

An orthopedic support material comprising:

(a) a water-curable resin composition containing less than about 1 wt-% of a solvent and having a viscosity of no greater than about 500 Pa-s under ambient conditions, said resin composition comprising:
(i) a water-reactive alkoxysilane terminated prepolymer having at least one hydrolyzable group per molecule;
and
(ii) an effective amount of a catalyst to catalyze the polymerization of said alkoxysilane terminated prepolymer upon contact with water,
wherein the water-reactive prepolymer is a compound of the formula:
##STR10## wherein:
(a) Q is a polyol residue;
(b) W is --NH--C(O)--X(R.sup.2.sub.2-n-q)-- or --X(R.sup.2.sub.2-n-q)--C(O)--NH--;
(c) X is --N--, --O--, or --S--;
(d) Y is --NH--, --O--, --S--, carbamylthio (--S--C(O)--NH--), carbamate (--O--C(O)--NH--), or unsubstituted or N-substituted ureido (--N(C(O)--NH--)--);
(e) R.sup.1 is a substituted or unsubstituted divalent bridging C.sub.1 -C.sub.200 hydrocarbon group, optionally interrupted in the backbone by 1-50 nonperoxide --O--, --C(O)--, --S--, --SO.sub.2 --, --N(R.sup.6)--, amide (--C(O)--NH--), ureido (--NH--C(O)--NH--), carbamate (--0--C(O)--NH--), carbamylthio (--S--C(O)--NH--), unsubstituted or N-substituted allophonate (--NH--C(O)--N(C(O)--O--)--), unsubstituted or N-substituted biuret (--NH--C(O)--N(C(O)--NH--)--), and N-substituted isocyanurate groups;
(f) R.sup.2 can be present or absent, and is selected from the group consisting of H and a substituted or unsubstituted C.sub.1 -C.sub.20 hydrocarbon group, optionally interrupted in the backbone by 1-10 nonperoxide --O--, --C(O)--, --S--, --SO.sub.2 --, or --N(R.sup.6)-- groups;
(g) R.sup.3 is a substituted or unsubstituted divalent bridging C.sub.3 -C.sub.20 hydrocarbon group, optionally interrupted in the backbone by 1-5 nonperoxide --O--, --C(O)--, --S--, --SO.sub.2 --, or--N(R.sup.6)-- groups;
(h) R.sup.4 is a C.sub.1 -C.sub.6 hydrocarbon group or --N.dbd.C(R.sup.7).sub.2 ;
(i) each R.sup.5 and R.sup.7 is independently a C.sub.1 -C.sub.6 hydrocarbon group;
(j) R.sup.6 is a H or a C.sub.1 -C.sub.6 hydrocarbon group;
(k) n=1-2 and q=0-1, with the proviso that when X is N, n+q=1, and when X is S or O, n+q=2;
(l) m=2-3;
(m) z=1-3;
and
(n) u=0, the functionality of the polyol residue=0-6, with the proviso that when u=0, the water-reactive prepolymer is a compound of formula ##STR11## wherein R.sup.1, W, R.sup.3, R.sup.4, R.sup.5, m, n, and z are as defined above.

18 more elements

Dependencies are inferred from the claim text.

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Abstract

An orthopedic casting material comprising:

(a) a water-curable resin composition containing less than about 1 wt-% of a solvent, said resin having a viscosity of no greater than about 500 Pa-s under ambient conditions, said resin composition comprising:
(i) a water-reactive alkoxysilane terminated prepolymer having at least one hydrolyzable group per molecule;
and
(ii) an effective amount of a catalyst to catalyze the polymerization of said alkoxysilane terminated prepolymer upon contact with water;
and
(b) a porous flexible substrate coated with the water-curable resin composition, wherein said orthopedic casting material is sufficiently porous to enable water to permeate a roll of said casting material during water activation and cause said resin to cure, and wherein said orthopedic casting material is sufficiently porous to allow air and moisture vapor to move through the material after it has been cured, wherein the water-reactive prepolymer is a compound of the formula;
##STR6## wherein:
(a) Q is a polyol residue;
(b) W is --NH--C(O)--X(R.sup.2.sub.2-n-q)-- or --X(R.sup.2.sub.2-n-q)--C(O)--NH--;
(c) X is --N--, --O--, or --S--;
(d) Y is --NH--, --O--, --S--, carbamylthio (--S--C(O)--NH--), carbamate (--O--C(O)--NH--), or unsubstituted or N-substituted ureido (--N(C(O)--NH--)--);
(e) R.sup.1 is a substituted or unsubstituted divalent bridging C.sub.1 -C.sub.200 hydrocarbon group, optionally interrupted in the backbone by 1-50 nonperoxide --O--, --C(O)--, --S--, --SO.sub.2 --, --N(R.sup.6)--, amide (--C(O)--NH--), ureido (--NH--C(O)--NH--), carbamate (--O--C(O)--NH--), carbamylthio (--S--C(O)--NH--), unsubstituted or N-substituted allophonate (--NH--C(O)--N(C(O)--NH--), unsubstituted or N-substituted biuret (--NH--C(O)--N(C(O)--NH--)--), and N-substituted isocyanurate groups;
(f) R.sup.2 can be present or absent, and is selected from the group consisting of H and a substituted or unsubstituted C.sub.1 -C.sub.20 hydrocarbon group, optionally interrupted in the backbone by 1-10 nonperoxide --O--, --C(O)--, --S--, --SO.sub.2 --, or --N(R.sup.6), groups;
(g) R.sup.3 is a substituted or unsubstituted divalent bridging C.sub.1 -C.sub.20 hydrocarbon group, optionally interrupted in the backbone by 1-5 nonperoxide --O--, --C(O)--, --S--, --SO.sub.2 --, or
(h) R.sup.4 is a C.sub.1 -C.sub.6 hydrocarbon group or --N.dbd.C(R.sup.7).sub.2 ;
(i) each R.sup.5 and R.sup.7 is independently a C.sub.1 -C.sub.6 hydrocarbon group;
(j) R.sup.6 is a H or a C.sub.1 -C.sub.6 hydrocarbon group;
(k) n=1-2 and q=0-1, with the proviso that when X is N, n+q=1, and when X is S or O, n+q=2;
(l) m=2-3;
(m) z=1-3;
and
(n) u=the functionality of the polyol residue=0-6, with the proviso that when u=0 the water-reactive prepolymer is a compound of formula ##STR7## wherein R.sup.1, W, R.sup.3, R.sup.4, R.sup.5, m, n, and z are as defined above.

19 more elements