Polymers of haloalkyl and haloalkenyl ether (meth)acrylates

Abstract

A curable composition containing at least one of a haloalkyl ether (meth)acrylate or a haloalkenyl ether (meth)acrylate and, optionally, one or more different types of co-monomers is cured to provide a polymer having advantageous properties as a result of the incorporation of halogenated functionality derived from the haloalkyl/haloalkenyl ether (meth)acrylate monomer.

What is claimed is: 
     
         1 . A polymer comprising, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I):
   X 1 X 2 HC—CX 3 X 4 —O—R—O—C(═O)—CR 1 ═CH 2   (I)
   
       wherein R is an organic moiety, X 1 , X 2 , X 3  and X 4  are independently selected from hydrogen, alkyl or haloalkyl, subject to the proviso that at least one of X 1 , X 2 , X 3  or X 4  is a C1-C8 haloalkyl group, at least one of X 1 , X 2 , X 3  or X 4  is a halogen and R 1  is hydrogen or methyl. 
     
     
         2 . The polymer of  claim 1 , wherein the polymer comprises, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I) wherein at least two of X 1 , X 2 , X 3  or X 4  are alkyl or haloalkyl group, at least two of X 1 , X 2 , X 3  or X 4  are halogen. 
     
     
         3 . The polymer of  claim 1 , wherein the polymer comprises, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I) wherein at least two of X 1 , X 2 , X 3  or X 4  are selected from the group consisting of fluorine and fluoroalkyl groups. 
     
     
         4 . The polymer of  claim 1 , wherein the polymer comprises, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I) wherein at least one of X 1 , X 2 , X 3  or X 4  is fluorine or a fluoroalkyl group. 
     
     
         5 . The polymer of  claim 1 , wherein the polymer comprises, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I) wherein each of X 1 , X 2 , X 3  and X 4  is halogen or a haloalkyl group. 
     
     
         6 . The polymer of  claim 1 , wherein the polymer comprises, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I) wherein R is an alkylene segment or a poly(oxyalkylene) segment. 
     
     
         7 . The polymer of  claim 1 , wherein the polymer comprises, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I) wherein R is an ethylene segment or a poly(oxyethylene) segment. 
     
     
         8 . The polymer of  claim 1 , wherein the polymer comprises, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I) wherein R is —[CH 2 CH 2 O] n —CH 2 CH 2 — and n is 0 or an integer of from 1 to 10. 
     
     
         9 . The polymer of  claim 1 , wherein the moiety X 1 X 2 HC—CX 3 X 4 —O—R—O— has a molecular weight not greater than 900 daltons. 
     
     
         10 . The polymer of  claim 1 , wherein R is a non-halogenated organic moiety. 
     
     
         11 . The polymer of  claim 1 , wherein R is an aliphatic organic moiety, optionally containing one or more oxygen atoms. 
     
     
         12 . The polymer of  claim 1 , wherein R is a saturated aliphatic organic moiety, optionally containing one or more ether oxygen atoms. 
     
     
         13 . The polymer of  claim 1 , wherein the polymer is a copolymer of a) said at least one haloalkyl ether (meth)acrylate and b) at least one (meth)acrylate-functionalized compound other than said haloalkyl ether (meth)acrylate comprising a haloalkyl moiety bonded through an ether linkage and an organic spacer moiety to a (meth)acrylate functional group. 
     
     
         14 . A polymer comprising, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I):
   X 1 X 2 HC—CX 3 X 4 —O—R—O—C(═O)—CR 1 ═CH 2   (I)
   
       wherein R is an organic moiety, X 1 , X 2 , X 3  and X 4  are independently selected from hydrogen, alkyl or haloalkyl, subject to the proviso that at least one of X 1 , X 2 , X 3  or X 4  is a C1-C8 fluororalkyl group, at least one of X 1 , X 2 , X 3  or X 4  is a halogen and R 1  is hydrogen or methyl. 
     
     
         15 . The polymer of  claim 14 , wherein the polymer comprises, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I) wherein at least two of X 1 , X 2 , X 3  or X 4  are alkyl or fluoroalkyl group, at least two of X 1 , X 2 , X 3  or X 4  are halogen. 
     
     
         16 . The polymer of  claim 14 , wherein the polymer comprises, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I) wherein at least two of X 1 , X 2 , X 3  or X 4  are selected from the group consisting of fluorine and fluoroalkyl groups. 
     
     
         17 . The polymer of  claim 14 , wherein the polymer comprises, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I) wherein each of X 1 , X 2 , X 3  and X 4  is halogen or a fluoroalkyl group. 
     
     
         18 . The polymer of  claim 14 , wherein the polymer comprises, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I) wherein R is an alkylene segment or a poly(oxyalkylene) segment. 
     
     
         19 . The polymer of  claim 14 , wherein the polymer comprises, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I) wherein R is an ethylene segment or a poly(oxyethylene) segment. 
     
     
         20 . The polymer of  claim 14 , wherein the polymer comprises, in polymerized form, at least one haloalkyl ether (meth)acrylate corresponding to general structure (I) wherein R is —[CH 2 CH 2 O] n —CH 2 CH 2 — and n is 0 or an integer of from 1 to 10. 
     
     
         21 . The polymer of  claim 14 , wherein the moiety X 1 X 2 HC—CX 3 X 4 —O—R—O— has a molecular weight not greater than 900 daltons. 
     
     
         22 . The polymer of  claim 14 , wherein R is a non-halogenated organic moiety. 
     
     
         23 . The polymer of  claim 14 , wherein R is an aliphatic organic moiety, optionally containing one or more oxygen atoms. 
     
     
         24 . The polymer of  claim 14 , wherein R is a saturated aliphatic organic moiety, optionally containing one or more ether oxygen atoms. 
     
     
         25 . The polymer of  claim 14 , wherein the polymer is a copolymer of a) said at least one haloalkyl ether (meth)acrylate and b) at least one (meth)acrylate-functionalized compound other than said haloalkyl ether (meth)acrylate comprising a haloalkyl moiety bonded through an ether linkage and an organic spacer moiety to a (meth)acrylate functional group. 
     
     
         26 . A curable composition comprising a) haloalkyl ether (meth)acrylate corresponding to general structure (I):
   X 1 X 2 HC—CX 3 X 4 —O—R—O—C(═O)—CR 1 ═CH 2   (I)
   
       wherein R is an organic moiety and at least one of X 1 , X 2 , X 3  and X 4  is selected from C1-C8 haloalkyl or C1-C8 fluoroalkyl, and b) at least one of i) a (meth)acrylate-functionalized compound other than said haloalkenyl ether (meth)acrylate or ii) a curing agent. 
     
     
         27 . The curable composition of  claim 26 , additionally comprising at least one co-monomer which is not said haloalkenyl ether (meth)acrylate.