Chain extended urethane dimethacrylate and dental impression formation

Claim 2

A new composition of matter comprising a compound of the general formula R 3 = H, alkyl, sub alkyl, aryl, sub aryl, F, CN. R 3 may be the same or different in each position. R 4 = Alkylene, sub alkylene, arylene or sub arylene having from 2 to 100 C. R 5 = Alkylene, sub alkylene, arylene, sub arylene; and A = a hydrocarbon substituent.

Claim 3

The new composition of matter of Claim 1 wherein said compounds provides that general formula A = R 6 - B - [R 6 ]n R 6 = Alkylene, sub alkylene, arylene, sub arylene or amine. n = 0 or 1 B = urethane (including polyurethanes) and R 6 - B are joined by a urethane linkage.

Claim 4

The new composition of matter of Claim 2 wherein said compounds general formula provides that B has at least two urethane linkages and R 2 has from 2 to 100 C, and is chosen from the group consisting of polyether, polyester or mixtures thereof and R 1 is methyl and R 4 is an alkylene having from 2 to 10C and A is preferably chosen from the group consisting of polyether, polyester or mixtures thereof.

Claim 5

A new composition of matter comprising a compound of the general formula R7 = Alkylene, sub alkylene; x = 10 to 100.

Claim 6

A new composition of matter comprising a compound of the general formula R7 = Alkylene, sub alkylene; x = 10 to 100.

Claim 7

The new composition of any one of Claims 1 through 4 wherein said composition is a dental impression material, non-toxic in use in the oral cavity, stable in storage for at least one (1) month as a one-component composition when actinic light free, and assumes a permanent elastomeric memory when exposed to light filtered to limited wave lengths within the visible light range for one (1) minute to a depth of one (1) inch.

Claim 8

The new composition of matter of any one of Claims 1 through 5 comprising an initiator activated by actinic light within the visible light range of about 360 to about 600 nanometers.

Claim 9

A method of producing a chain extended urethane polyacrylate suitable for producing composition of Claim 1 comprising reacting a polyhydroxy compound with a polyisocyanate and forming a first reaction product having about 2 equivalents of reactive isocyanate, reacting said first reaction product with less than two equivalents of compound having an acryl pendent radical and another reactive site preferentially reacting with said first reaction product to form a second reaction product, reacting said second reaction product with a compound chosen from the group consisting of polyhydroxy alkylene, sub alkylene, arylene, sub arylene, oxyalkylene or sub oxyalkylene and amine to form a third reaction product and reacting said third reaction product with an isocyanto acryl.

Claim 10

.8. The method of Claim 7 wherein said reacting of said first reaction product with said compound having an acryl pendent radical and another reactive site preferentially reacting with said first reaction products caps a portion of said reactive isocyanate leaving other reactive pendent isocyanate reaction sites in said second reaction products and leaving a pendent acryl reaction site on at least a substantial portion of the reaction molecular yield of said second reaction product and said reacting of said second reaction product with said compound chosen from said group is a chain extending reaction at least predominantly capping said other pendent reactive isocyanate.

Claim 11

The method of Claim 8 wherein the first polyhydroxy compound is a dihydroxy oxyalkylene and said second polyhydroxy compound is a dihydroxy alkylene and said isocyanate acryl is isocyanato alkylene acrylate.

Claim 12

The method of Claim 9 wherein said isocyanato alkylene acrylate is isocyanatoethyl methacrylate.

Claim 13

The method of Claim 7 wherein the first said polyhydroxy compound has about two reactive hydroxy equivalents and the first said isocyanate has about four reactive equivalents of isocyanate and said first reaction product has a molecular yield having about two remaining reactive isocyanate equivalents, said acrvl pendent radical containing compound is a mon acrylate and said other reactive site preferentially reacting with said first reaction product reacts preferentially with said remaining reactive isocyanate and said acryl pendent radical containing compound is present in an amount of about one equivalent of said other reactive sites to two equivalents of remaining reactive isocyanate and said second reaction product has a molecular yield having about one remaining reactive isocyanate equivalent, the compound chosen from said group being a dihydroxy compound present in an amount of about two reactive equivalents and yielding a third reaction product having a molecular yield having about one reactive equivalent that preferentially and said isocyanato acryl being present in its recited reaction in an isocyanate equivalent of about 1.