Multifunctional monomers, methods for making multifunctional monomers, polymerizable compostions and products formed thereform
First Claim
1. A method of making a multifunctional methylene malonate monomer comprising:
- (a) reacting at least one methylene malonate monomer with a diol, a polyol or a polymeric resin having at least two hydroxyl groups in the presence of an enzymatic catalyst to form a reaction complex wherein the at least one methylene malonate monomer is provided in an excess amount with respect to the diol, polyol or polymeric resin having at least two hydroxyl groups; and
(b) recovering multifunctional methylene malonate monomer comprising more than one methylene malonate core formula linked by the diol, polyol or polymeric resin having at least two hydroxyl groups from the reaction complex;
(c) adding a stabilizer to the reaction complex formed in step (a);
wherein in step (a) the at least one methylene malonate monomer is provided in an excess amount with respect to the diol, polyol or polymeric resin having at least two hydroxyl groups,recovering multifunctional methylene malonate monomer in step (b) includes separating the multifunctional methylene malonate monomer from the excess methylene malonate monomer and the diol, polyol or polymeric resin having at least two hydroxyl groups; and
the diol, polyol or polymeric resin having at least two hydroxyl groups correspond to the formula (HO)-[A]-(OH)m wherein;
[A] is independently selected from —
(CRARB)n—
, —
(CRARB)n—
O(C═
O)—
(CH2)1-15—
(C═
O)O—
(CRARB)n—
, —
(CH2)n—
[CY]—
(CH2)n, a polybutadienyl linking group, a polyethylene glycol linking group, a polyether linking group, a polyurethane linking group, an epoxy linking group, a polyacrylic linking group, or a polycarbonate linking group;
each instance of RA or RB is independently selected from H, C1-C15 alkyl, a moiety corresponding to the formula;
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Accused Products
Abstract
The present invention provides multifunctional monomers, including, but not limited to include multifunctional methylene malonate and methylene beta-ketoester monomers; methods for producing the same; and compositions and products formed therefrom. The multifunctional monomers of the invention may be produced by transesterification or by direct synthesis from monofunctional methylene malonate monomers or methylene beta-ketoester monomers. The present invention further compositions and products formed from methylene beta-ketoester monomers of the invention, including monomer-based products (e.g., inks, adhesives, coatings, sealants or reactive molding) and polymer-based products (e.g., fibers, films, sheets, medical polymers, composite polymers and surfactants).
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Citations
20 Claims
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1. A method of making a multifunctional methylene malonate monomer comprising:
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(a) reacting at least one methylene malonate monomer with a diol, a polyol or a polymeric resin having at least two hydroxyl groups in the presence of an enzymatic catalyst to form a reaction complex wherein the at least one methylene malonate monomer is provided in an excess amount with respect to the diol, polyol or polymeric resin having at least two hydroxyl groups; and (b) recovering multifunctional methylene malonate monomer comprising more than one methylene malonate core formula linked by the diol, polyol or polymeric resin having at least two hydroxyl groups from the reaction complex; (c) adding a stabilizer to the reaction complex formed in step (a);
wherein in step (a) the at least one methylene malonate monomer is provided in an excess amount with respect to the diol, polyol or polymeric resin having at least two hydroxyl groups,recovering multifunctional methylene malonate monomer in step (b) includes separating the multifunctional methylene malonate monomer from the excess methylene malonate monomer and the diol, polyol or polymeric resin having at least two hydroxyl groups; and
the diol, polyol or polymeric resin having at least two hydroxyl groups correspond to the formula (HO)-[A]-(OH)m wherein;[A] is independently selected from —
(CRARB)n—
, —
(CRARB)n—
O(C═
O)—
(CH2)1-15—
(C═
O)O—
(CRARB)n—
, —
(CH2)n—
[CY]—
(CH2)n, a polybutadienyl linking group, a polyethylene glycol linking group, a polyether linking group, a polyurethane linking group, an epoxy linking group, a polyacrylic linking group, or a polycarbonate linking group;each instance of RA or RB is independently selected from H, C1-C15 alkyl, a moiety corresponding to the formula; - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 19, 20)
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13. A method of making a multifunctional methylene malonate monomer comprising:
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(a) reacting at least one methylene malonate monomer having disubstituted vinyl functionality with a diol, a polyol or a polymeric resin having at least two hydroxyl groups and which does not have functional groups that react with the disubstituted vinyl functionality on the methylene malonate monomer, in the presence of an enzymatic catalyst to form a reaction complex;
wherein the at least one methylene malonate monomer is provided in an excess amount with respect to the diol, polyol or polymeric resin having at least two hydroxyl groups; and(b) recovering multifunctional methylene malonate monomer comprising more than one methylene malonate core formula linked by the diol, polyol or polymeric resin having at least two hydroxyl groups from the reaction complex, (c) adding a stabilizer to the reaction complex formed in step (a); recovering multifunctional methylene malonate monomer in step (b) includes separating the multifunctional methylene malonate monomer from the excess methylene malonate monomer and the diol, polyol or polymeric resin having at least two hydroxyl groups. - View Dependent Claims (14, 15, 16, 17, 18)
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Specification