ELECTRON DEFICIENT OLEFINS

1 . Compounds embraced by structure I

wherein X is (a) an electron withdrawing group, or (b) Y;

Y is

wherein D is a member selected from the group consisting of H, alkyl and aryl,

Z is either

(i)

wherein Q is

a. an electron withdrawing group or

b. a first reactive functionality, or

(ii) a second reactive functionality, g is 1-10; and

n is 0 or 1.

2 . Compounds according to claim 1 , wherein X is an electron withdrawing group selected from the group consisting of CN, CO 2 R, CO 2 H, COCl, COR, COPO(OR) 2 , COPOR 2 , SO 2 R, SO 3 R and NO 2 , wherein R is C 1-4 .

3 . Compounds according to claim 1 , wherein Y is

wherein D is a member selected from the group consisting of H, alkyl and aryl, Z is

wherein Q is an electron withdrawing group selected from the group consisting of CN, CO 2 R, CO 2 H, COCl, COR, COPO(OR) 2 , COPOR 2 , SO 2 R, SO 3 R and NO 2 , wherein R is C 1-4 , and g is 1.

4 . Compounds according to claim 1 , wherein Y is

wherein D is a member selected from the group consisting of H, alkyl and aryl, Z is

wherein Q is a first reactive functionality selected from the group consisting of amides and thioamides and g is 1.

5 . Compounds according to claim 1 , wherein Y is

wherein D is a member selected from the group consisting of H, alkyl and aryl, Z is a second reactive functionality selected from the group consisting of epoxides, episulfides, oxetanes, thioxetanes, dioxolanes, dioxanes, isocyanates, maleimides, oxazolines, succinimides, 2-cyanoacrylates, methylidene malonates, acrylonitrile, (meth)acrylates, carboxylic acids and derivatives thereof, cyanoacetates, methylene malonates, hydroxyls, silanes, siloxanes, titanates, and zirconates, and g is 1.

6 . Compounds according to claim 1 , embraced by structure II

wherein X is an electron withdrawing group or E, E is as shown,

is a reactive functionality, D is a member selected from the group consisting of H, alkyl and aryl, n is 0 or 1, g is 1, and A, B, 1, 2, 3, 4, 5, and 6 are each references to bond designations.

7 . Compounds according to claim 1 , embraced by structure III

wherein X is an electron withdrawing group or F, D is a member selected from the group consisting of H, alkyl and aryl, Z is a reactive functionality, n is 0 or 1 and g is 1.

8 . Compounds according to claim 7 , wherein Z is a second reactive, functionality selected from the group consisting of epoxides, episulfides, oxetanes, thioxetanes, dioxolanes, dioxanes, isocyanates, maleimides, oxazolines, succinimides, 2-cyanoacrylates, methylidene malonates, acrylonitrile, (meth)acrylates, carboxylic acids and derivatives thereof, cyanoacetates, methylene malonates, hydroxyls, silanes, siloxanes, titanates, and zirconates.

9 . Compounds according to claim 1 , selected from the group consisting of

10 . A composition comprising:

(a) one or more compounds of claim 1 ;

(b) a stabilizer package comprising at least one of a free radical stabilizer and an anionic stabilizer; and

(c) optionally, one or more additives selected from the group consisting of cure accelerators, thickeners, thixotropes, tougheners, thermal resistance-conferring agents, and plasticizers.

11 . The composition of claim 10 , further comprising a cyanoacrylate within structure IV:

wherein R 1 is selected from C 1-16 alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, arylalkyl, aryl, allyl and haloalkyl groups.

12 . The composition of claim 11 , wherein the cyanoacrylate is selected from methyl cyanoacrylate, ethyl-2-cyanoacrylate, propyl cyanoacrylates, butyl cyanoacrylates, octyl cyanoacrylates, allyl cyanoacrylate, β-methoxyethyl cyanoacrylate and combinations thereof.

13 . The composition of claim 10 , further comprising a methylidene malonate within structure V:

wherein R 2 and R 3 are each independently selected from C 1-16 alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, arylalkyl, aryl, allyl and haloalkyl groups.

14 . A composition comprising:

(a) one or more compounds of claim 9 ;

(b) a stabilizer package comprising at least one of a free radical stabilizer and an anionic stabilizer; and

(c) optionally, one or more additives selected from the group consisting of cure accelerators, thickeners, thixotropes, tougheners, thermal resistance-conferring agents, and plasticizers.

15 . The composition of claim 14 , further comprising a coreactant.

16 . The composition of claim 15 , wherein the coreactant is a member selected from the group consisting of epoxides, episulfides, oxetanes, thioxetanes, dioxolanes, dioxanes, isocyanates, maleimides, oxazolines, (meth)acrylates, acrylamides, cyanoacrylates, methylidene malonates, and vinyl ethers.

17 . Compounds according to claim 4 , wherein the amides or thioamides of Q are embraced by

C(T)NUV,

wherein T is O or S and U or V are each independently selected from H or R, wherein R is C 1-4 .