Curable polymeric materials and methods of using same
View Patent ↗Polymeric materials are disclosed herein that include a Polymer A, a Polymer B, and an oxalate ester or reaction product thereof. Polymer A contains electrophilic reactive groups, and Polymer B contains nucleophilic groups. In certain embodiments, the polymeric materials are free-flowing liquids at 100% solids that can be used, for example, as topical skin adhesives.
1. A two-part reactive composition comprising:
a) a first part comprising Polymer A and a compound of Formula (IV), a compound of Formula (V), or both,
wherein Polymer A comprises:
a plurality of first monomeric units of Formula (I):
wherein:
each R 1 is independently hydrogen or methyl;
each R 2 and R 3 are independently a linear or branched alkyl having 4 to 14 carbon atoms; and
a plurality of second monomeric units of Formula (II), Formula (III), or a mixture thereof:
wherein the compounds of Formula (IV) or Formula (V) are of the formulas:
R 4 O—(CO)—(CO)—OR 4 (IV)
R 4 O—(CO)—(CO)—NH—R 5 —NH—(CO)—(CO)—OR 4 (V),
wherein:
each R 4 is independently alkyl, aralkyl, substituted aralkyl, alkenyl, aryl, substituted aryl; and
each R 5 is independently a divalent hydrocarbon linking group that may optionally include heteroatoms; and
b) a second part comprising Polymer B, wherein Polymer B comprises:
at least 80 weight percent of a plurality of first monomeric units of Formula (I):
wherein:
each R 1 is independently hydrogen or methyl;
independently R 2 and R 3 are independently a linear or branched alkyl having 4 to 14 carbon atoms; and
a plurality of monomeric units having a primary amino group.
2. The two-part reactive composition of claim 1 , wherein Polymer A comprises a range of 25 to 93 weight percent of the monomeric units of Formula (I).
3. The two-part reactive composition of claim 1 , wherein Polymer A further comprises a monomeric unit comprising a siloxane group.
4. The two-part reactive composition of claim 1 , wherein Polymer A further comprises a monomeric unit formed from a monomer comprising an acidic group selected from the group consisting of acrylic acid, 2-carboxyethyl acrylate, 2-carboxyethyl acrylate oligomers, and combinations thereof.
5. The two-part reactive composition of claim 1 , wherein Polymer A further comprises a monomeric unit comprising a plurality of (meth)acryloyl groups.
6. The two-part reactive composition of claim 1 , wherein Polymer A has a weight average molecular weight (M w ) in a range of 10,000 Daltons to 100,000 Daltons.
7. The two-part reactive composition of claim 6 , wherein the first part further comprises an oligomeric or polymeric additive having a weight average molecular weight (Mw) of less than 10,000 Daltons.
8. The two-part reactive composition of claim 7 , wherein the oligomeric or polymeric additive comprises:
a plurality of first monomeric units of Formula (I):
wherein:
each R 1 is independently hydrogen or methyl;
each R 2 and R 3 are independently a linear or branched alkyl having 4 to 14 carbon atoms; and
a plurality of second monomeric units of Formula (II), Formula (III), or a mixture thereof:
9. The two-part reactive composition of claim 1 , wherein Polymer B has a weight average molecular weight (M w ) of at least 12,000 Daltons and a weight average molecular weight (M w ) of no greater than 100,000 Daltons.
10. The two-part reactive composition of claim 1 , wherein a monomeric unit of the plurality of monomeric units of Polymer B having a primary amino group is a reaction product of a diamine with a monomeric unit formed from maleic anhydride or a monomeric unit formed from vinyl dimethyl azlactone.
11. The two-part reactive composition of claim 1 , wherein the second part further comprises an amine additive different than Polymer B.
12. A multi-chambered mixing and/or dispensing device containing the two-part reactive composition of claim 1 , wherein the first part is present in a first chamber of the multi-chambered mixing and/or dispensing device, and the second part is present in a second chamber of the multi-chambered mixing and/or dispensing device.
13. A method of preparing a polymeric material comprising:
providing a two-part reactive composition according to claim 1 ; and
combining the first part and the second part under conditions effective for the reaction of the first part and the second part to form the polymeric material.
14. The method of claim 13 , wherein conditions effective for the reaction of the first part and the second part to form the polymeric material comprise room temperature or body temperature.