Free radically polymerizable siloxanes and siloxane polymers
Assignee3M Innovative Properties Company
InventorsPaul E. Humpal, Audrey A. Sherman, Mieczyslaw H. Mazurek, Bradley A. Craig
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Abstract
Free radically polymerizable synthons for preparing siloxane polyoxamide copolymers are prepared by reacting amine-terminated siloxane polyoxamide compounds with an isocyanate-functional (meth)acrylate, an isocyanate-functional vinyl-substituted aromatic compound, or a vinyl azlactone. These free radically polymerizable synthons can be used to prepare polymer compositions by combining the free radically polymerizable synthons with an initiator and initiating polymerization.
Claims20
A free radically polymerizable compound comprising the formula:
- X—[—R3N—Z—NR3]—{—(CO)(CO)—[NH—Y—Sir12—(OSir12)n—OSir12—Y—NH—(CO)(CO)—]p—[—R3N—Z—NR3]—}r—X
- wherein each R1 is independently an alkyl, haloalkyl, aralkyl, aryl, or aryl substituted with an alkyl, alkoxy, or halo;
- each Y is independently a divalent alkylene, aralkylene, or a combination thereof;
- each Z is independently a divalent or higher-valent polydiorganosiloxane, alkylene, aralkylene, heteroalkylene, or branched alkylene group;
- each R3 is hydrogen or alkyl or R3 taken together with Z and with the nitrogen to which they are both attached forms a heterocyclic group;
- each X is independently a free radically polymerizable group;
- n is independently an integer of 0 to 1500;
- p is an integer of 1 or greater;
- and
- r is an integer of 1 or greater.
A method of making a free radically polymerizable compound comprising mixing together under reaction conditions:
- a compound of the formula:
- H—[—R3N—Z—NR3]—{—(CO)(CO)—[NH—Y—Sir12—(OSir12)n—OSir12—Y—NH—(CO)(CO)—]p—[—R3N—Z—NR3]—}r—H
- wherein each R1 is independently an alkyl, haloalkyl, aralkyl, aryl, or aryl substituted with an alkyl, alkoxy, or halo;
- each Y is independently a divalent alkylene, aralkylene, or a combination thereof;
- each Z is independently a divalent or higher-valent polydiorganosiloxane, alkylene, aralkylene, heteroalkylene, or branched alkylene group;
- each R3 is hydrogen or alkyl or R3 taken together with Z and with the nitrogen to which they are both attached forms a heterocyclic group;
- n is independently an integer of 0 to 1500;
- p is an integer of 1 or greater;
- and
- r is an integer of 1 or greater;
- and
- an amine-reactive compound, wherein the amine-reactive compound comprises an isocyanate-functional (meth)acrylate, an isocyanate-functional vinyl-substituted aromatic compound, or a vinyl azlactone.
A polymer composition comprising a polymer prepared from a reaction mixture comprising:
- a free radically polymerizable compound comprising the formula:
- X—[—R3N—Z—NR3]—{—(CO)(CO)—[NH—Y—Sir12—(OSir12)n—OSir12—Y—NH—(CO)(CO)—]p—[—R3N—Z—NR3]—}r—X
- wherein each R1 is independently an alkyl, haloalkyl, aralkyl, aryl, or aryl substituted with an alkyl, alkoxy, or halo;
- each Y is independently a divalent alkylene, aralkylene, or a combination thereof;
- each Z is independently a divalent or higher-valent polydiorganosiloxane, alkylene, aralkylene, heteroalkylene, or branched alkylene group;
- each R3 is hydrogen or alkyl or R3 taken together with Z and with the nitrogen to which they are both attached forms a heterocyclic group;
- each X is independently a free radically polymerizable group;
- n is independently an integer of 0 to 1500;
- p is an integer of 1 or greater;
- and
- r is an integer of 1 or greater;
- and
- an initiator.
Dependencies are inferred from the claim text.