Bisphenol A-Free Crosslinked Polymer Composition
The present application discloses improved BPA-free crosslinked polymers comprising a bis-electrophile and a polynucleophile, useful in commercial employment as can linings and such. Exemplary embodiments comprise a dianhydride and a polyol, a bis-phenol (other than BPA) and a polyepoxide, a bis-epoxide and a polyphenol, and a bis-styrene and an unsaturated polyester.
1 . A spray composition for a can lining comprising a polynucleophile and a bis-electrophile.
2 . The composition of claim 1 wherein the polynucleophile/bis-electrophile pair is selected from the group consisting of polyol/dianhydride, polyphenol/bis-epoxide, polyepoxide/bisphenol, and unsaturated polyester/bis-styrene.
3 . The composition of claim 2 comprising a polyol and a dianhydride.
4 . The composition of claim 3 wherein the dianhydride is selected from the group consisting of benzophenone-3,3′,4,4′-tetracarboxylic dianhydride, 4,4′-oxydiphthalic anhydride, 4,4′-biphthalic anhydride, and bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride.
5 . The composition of claim 3 wherein the polyol is selected from the group consisting of polyvinyl alcohols (PVA), styrene-allyl alcohol copolymers (SAA), polyvinyl butyrals (PVB), ethylene vinyl alcohol copolymers, 1,4-butanediol, 1,3-propanediol, 1,6-hexanediol, diethylene glycol, 1,1,1-tris(hydroxymethyl)propane, triethanolamine and mixtures of same, diols and triols.
6 . The composition of claim 2 comprising a polyphenol and a bis-epoxide.
7 . The composition of claim 6 wherein the polyphenol has the structure of formula I:
wherein n, m, and p are integers together denoting the fraction of each monomer or group in the polymer;
o=1, 2 or 3; and
R 1 , R 2 , and R 3 are independently selected from the group consisting of H and C 1-8 linear or branched alkyl.
8 . The composition of claim 6 wherein the bis-epoxide has the structure of formula VII:
wherein A is selected from the group consisting C 1-20 linear or branched alkyl, or C 3-20 cyclyl, heterocyclyl, aryl or heteroaryl.
9 . The composition of claim 2 comprising a polyepoxide and a bisphenol.
10 . The composition of claim 9 wherein the polyepoxide has the structure of formula II:
11 . The composition of claim 9 wherein the bisphenol has the structure of formula VIII:
wherein A is selected from the group consisting of C 1-20 linear or branched alkyl, or C 3-20 cyclyl, heterocyclyl, aryl or heteroaryl, and further wherein A is not —C(CH 3 ) 2 —.
12 . The composition of claim 2 comprising an unsaturated polyester and a bis-styrene.
13 . The composition of claim 12 wherein the unsaturated polyester is selected from the structures of formulae IV, V and VI:
wherein
n, m, and p are integers together denoting the fraction of each monomer or group in the polymer.
14 . The composition of claim 12 wherein the bis-styrene has the structure of formula IX:
wherein A is selected from the group consisting of C 1-20 linear or branched alkyl, or C 3-20 cyclyl, heterocyclyl, aryl or heteroaryl.
15 . A bis-epoxide selected from the group consisting of:
16 . A bisphenol selected from the group consisting of:
17 . A bis-styrene selected from the group consisting of:
18 . An unsaturated polyester polymer selected from the structures of formulae IV, V and VI:
wherein
n, m, and p are integers together denoting the fraction of each monomer or group in the polymer.
19 . A composition comprising: (a) a bis-electrophile; (c) a polynucleophile; and (d) an accelerator.
20 . A method of making a crosslinked polymer, the method comprising the steps of:
a. dissolving a bis-electrophile in a solvent to form a solution,
b. optionally adding an accelerator to the solution,
c. after steps (a) and (b), adding a polynucleophile to the solution, and then
d. stirring the resultant solution.
21 . A crosslinked polymer made by the method of claim 20 .