Iron(II) containing complex and condensation reaction catalysts, methods for preparing the catalysts, and compositions containing the catalysts
View Patent ↗A composition is capable of curing via condensation reaction. The composition uses a new condensation reaction catalyst. The new condensation reaction catalyst is used to replace conventional tin catalysts. The composition can react to form a gum, gel, rubber, or resin.
1. A composition comprising ingredients (A) and (B): where Ingredient (A) is a catalytically effective amount of a reaction product of a Fe(II) precursor and a ligand, where the Fe(II) precursor is distinct from the reaction product of the Fe(II) precursor and the ligand, and where the ligand is one of general formulae (ii), (iii), (iv), (v), (vi), (vii), (xiii), (xvi), (xvii), (xviii), (xix), (xx), (xxi), or (xxii), or one of ligands 5, 10, 23, 32, 33, 37, 41, 42, 43, 44, 50, 56, 58, 66, 68, 76, 78, 81, 83, 100, 101, 103, 105, 108, 109, 110, 112, 113, 114, 115, 116, 118, 122, 123, 125, 131, 141, 154, 168, 169, 171, 172, 173, 174, 175, 177, 178, 179, 188, 189, 192, 208, 231, 233, 234, 239, 240, 250, 260, 264, 267, 268, 276, 277, 278, 279, 280, 281, 283, 284, 285; where
General formula (ii) is
where subscript a is an integer from 0 to 4, Q 1 is selected from O and S, A 1 and each A 3 are each independently selected from H, monovalent organic group, a halogen, and an inorganic group, with the proviso that when subscript a>1, then A 3 may form a ring structure with another A 3 , A 2 is a monovalent organic group with the proviso that A 2 may form a bridged structure with an ethylene bridge to another structure (ii), and with the proviso A 2 is not mesityl; or
General formula (iii) is
where subscript b is an integer from 0 to 4, Q 2 is selected from OH and SA 14 , where A 14 is selected from H, monovalent organic group, a halogen, and an inorganic group, Q 4 is selected from O, S, and C, Q 3 is selected from N and C, A 11 is selected from H, monovalent organic group, a halogen, and an inorganic group, each A 13 is independently selected from a monovalent organic group, a halogen, and an inorganic group, with the proviso that when b>1, then A 13 may form a ring structure with another A 13 , and A 12 and A 10 are each independently selected from H, monovalent organic group, a halogen, an inorganic group, and nothing; or
General formula (iv) is
where Q 5 is selected from O and S, A 21 , A 23 , A 22 , and A 20 are each independently selected from H, monovalent organic group, a halogen, and an inorganic group, A 24 is selected from H and a monovalent organic group; with the provisos that A 20 and A 21 may combine to form a ring structure and/or A 22 and A 21 may combine to form a ring structure and/or A 23 and A 24 may combine to form a ring structure; or
General formula (v) is
where subscript c is an integer from 0 to 4, each A 33 is independently selected from a monovalent organic group, a halogen, and an inorganic group, with the proviso that when c>1, then A 33 may form a ring structure with another A 33 , and A 31 and A 32 are each independently selected from H and a monovalent organic group; or
General formula (vi) is
where Q 8 is selected from O and S, Q 9 is selected from N and P, subscript d is an integer from 0 to 4, each A 43 is independently selected from a monovalent organic group, a halogen, and an inorganic group, with the proviso that when d>1, then A 43 may form a ring structure with another A 43 , A 41 , A 44 , and A 40 are each independently selected from H and a monovalent organic group with the proviso that A 40 and A 44 are not mesityl or methylphenol, and A 42 is selected from H, a monovalent organic group, a halogen, and an inorganic group; or
General formula (vii) is
where subscript e is an integer from 0 to 4, each A 53 is independently selected from a monovalent organic group, a halogen, and an inorganic group, with the proviso that when e>1, then A 53 may form a ring structure with another A 53 , and A 52 and A 51 are each independently selected from H, monovalent organic group, a halogen, and an inorganic group, with the proviso that A 51 and A 52 may combine to form a ring structure; or
General formula (xiii) is
where A 111 is selected from H, monovalent organic group, a halogen and an inorganic group, and A 102 is selected from H and a monovalent organic group; or
General formula (xvi) is
where subscript t is an integer from 0 to 3, subscript u is an integer from 1 to 3, and each A 141 and each A 142 are independently selected from a monovalent organic group, a halogen, and an inorganic group; or
General formula (xvii) is
where subscript w is an integer from 0 to 4, each A 151 is independently selected from a monovalent organic group, a halogen and an inorganic group, and A 152 and A 153 are each independently selected from a monovalent organic group, a halogen and an inorganic group; or
General formula (xviii) is
where subscript x is an integer from 0 to 4, each A 161 is independently selected from a monovalent organic group, a halogen, and an inorganic group, and A 162 , A 163 , and A 164 are each independently a monovalent organic group;
General formula (xix) is
where subscript aa is an integer from 0 to 4, subscript bb is an integer from 0 to 4, each A 171 is independently selected from a monovalent organic group, a halogen and an inorganic group, each A 172 is independently selected from a monovalent organic group, a halogen and an inorganic group, and A 173 and A 174 are each independently a monovalent organic group; or
General formula (xx) is
where subscript cc is an integer from 0 to 4, each A 181 is independently selected from a monovalent organic group, a halogen, and an inorganic group, and A 182 is a monovalent organic group; or
General formula (xxi) is
where subscript dd is an integer from 0 to 4, each A 191 is independently selected from a monovalent organic group, a halogen, and an inorganic group, A 192 , A 194 , and A 195 are each independently a monovalent organic group, and A 193 is selected from a monovalent organic group, H, a halogen, and an inorganic group; or
General formula (xxii) is
where subscript ee is an integer from 0 to 4, each A 201 is independently selected from a monovalent organic group, a halogen, and an inorganic group, and A 202 is selected from a monovalent organic group, H, a halogen, and an inorganic group; or
Ingredient (B) is a silicon containing base polymer having an average, per molecule, of one or more hydrolyzable substituents, and
Ingredient (A) is capable of catalyzing a condensation reaction of the hydrolyzable substituents on ingredient (B).
2. The composition of claim 1 , where the Fe precursor has general formula Fe-A 2 , where each A is independently a monovalent organic group.
3. The composition of claim 2 , where one of conditions (a) to (c) is satisfied, where:
Condition (a) is each A is an ester group; or
Condition (b) is each A is stearate; or
Condition (c) is each A is acetate.
4. The composition of claim 2 , where one of conditions (A) and (B) is satisfied, where:
Condition (A) is the ligand is selected from the group consisting of ligands 5, 10, 23, 32, 33, 37, 41, 42, 43, 44, 50, 56, 58, 66, 68, 76, 78, 80, 81, 83, 100, 101, 103, 105, 108, 109, 110, 113, 114, 115, 116, 118, 122, 123, 125, 131, 141, 154, 168, 169, 171, 172, 173, 174, 175, 177, 178, 179, 188, 189, 192, and 208; or
Condition (B) is the ligand is selected from the group consisting of ligands 234, 239, 240, 250, 268, and 285.
5. The composition of claim 2 , where one of conditions (I) to (V) is satisfied, where
Condition (I) is that each A is an ester group, and the ligand is one of 5, 10, 23, 32, 33, 37, 41, 42, 43, 44, 50, 56, 58, 66, 68, 76, 78, 80, 81, 83, 100, 101, 103, 105, 108, 109, 110, 113, 114, 115, 116, 118, 122, 123, 125, 131, 141, 154, 168, 169, 171, 172, 173, 174, 175, 177, 178, 179, 188, 189, 192, 208, 234, 239, 240, 250, 268, or 285 in Table 1; or
Condition (II) is that each A is a stearate group, and the ligand is one of 5, 10, 23, 32, 33, 37, 41, 42, 43, 44, 50, 56, 58, 66, 68, 76, 78, 80, 81, 83, 100, 101, 103, 105, 108, 109, 110, 113, 114, 115, 116, 118, 122, 123, 125, 131, 141, 154, 168, 169, 171, 172, 173, 174, 175, 177, 178, 179, 188, 189, 192, or 208 in Table 1; or
Condition (III) is that each A is an acetate group and the ligand is one of 227, 230, 231, 233, 234, 239, 240, 250, or 285 in Table 1; or
Condition (IV) is that each A is a stearate group, and the ligand has one of general formulae (ii), (iii), (iv), (v), (vi), (vii), (xix), (xx), (xxi), or (xxii); or
Condition (V) is that each A is an acetate group, and the ligand has one of general formulae (xiii), (xvi), (xvii), or (xviii).
6. The composition of claim 1 , further comprising at least one additional ingredient distinct from ingredients (A) and (B), where the at least one additional ingredient is selected from the group consisting of: (C) a crosslinker; (D) a drying agent; (E) an extender, a plasticizer, or a combination thereof; (F) a filler; (G) a treating agent; (H) a biocide; (J) a flame retardant; (K) a surface modifier; (L) a chain lengthener; (M) an endblocker; (N) a nonreactive binder; (O) an anti-aging additive; (P) a water release agent; (Q) a pigment; (R) a rheological additive; (S) a vehicle; (T) a tackifying agent; (U) a corrosion inhibitor; and a combination thereof.
7. The composition of claim 1 , where the condensation reaction produces a reaction product having a visual viscosity value ranging from 2 to 5 when tested according to the method of Example 2.
8. A method for making the composition of claim 1 comprising: mixing ingredients comprising ingredient (A) and ingredient (B) so as to make the composition.
9. A method comprising: exposing the composition of claim 1 to moisture to prepare a reaction product.
10. The reaction product prepared by the method of claim 9 , where the reaction product has a form selected from a gum, a gel, a rubber, and a resin.
11. A method comprising: reacting
i) a Fe precursor of general formula Fe-A 2 , where each A is independently a monovalent organic group; and
ii) a ligand with one of general formulae (ii), (iii), (iv), (v), (vi), (vii), (xiii), (xvi), (xvii), (xviii), (xix), (xx), (xxi), or (xxii) or one of ligands 5, 10, 23, 32, 33, 37, 41, 42, 43, 44, 50, 56, 58, 66, 68, 76, 78, 81, 83, 100, 101, 103, 105, 108, 109, 110, 112, 113, 114, 115, 116, 118, 122, 123, 125, 131, 141, 154, 168, 169, 171, 172, 173, 174, 175, 177, 178, 179, 188, 189, 192, 208, 234, 239, 240, 250, 268, or 285; where
General formula (ii) is
where subscript a is an integer from 0 to 4, Q 1 is selected from O and S, A 1 and each A 3 are each independently selected from H, monovalent organic group, a halogen, and an inorganic group, with the proviso that when subscript a>1, then A 3 may form a ring structure with another A 3 , A 2 is a monovalent organic group with the proviso that A 2 may form a bridged structure with an ethylene bridge to another structure (ii), and with the proviso A 2 is not mesityl; or
General formula (iii) is
where subscript b is an integer from 0 to 4, Q 2 is selected from OH and SA 14 , where A 14 is selected from H, monovalent organic group, a halogen, and an inorganic group, Q 4 is selected from O, S, and C, Q 3 is selected from N and C, A 11 is selected from H, monovalent organic group, a halogen, and an inorganic group, each A 13 is independently selected from a monovalent organic group, a halogen, and an inorganic group, with the proviso that when b>1, then A 13 may form a ring structure with another A 13 , and A 12 and A 10 are each independently selected from H, monovalent organic group, a halogen, an inorganic group, and nothing; or
General formula (iv) is
where Q 5 is selected from O and S, A 21 , A 23 , A 22 , and A 20 are each independently selected from H, monovalent organic group, a halogen, and an inorganic group, A 24 is selected from H and a monovalent organic group; with the provisos that A 20 and A 21 may combine to form a ring structure and/or A 22 and A 21 may combine to form a ring structure and/or A 23 and A 24 may combine to form a ring structure; or
General formula (v) is
where subscript c is an integer from 0 to 4, each A 33 is independently selected from a monovalent organic group, a halogen, and an inorganic group, with the proviso that when c>1, then A 33 may form a ring structure with another A 33 , and A 31 and A 32 are each independently selected from H and a monovalent organic group; or
General formula (vi) is
where Q 8 is selected from O and S, Q 9 is selected from N and P, subscript d is an integer from 0 to 4, each A 43 is independently selected from a monovalent organic group, a halogen, and an inorganic group, with the proviso that when d>1, then A 43 may form a ring structure with another A 43 , A 41 , A 44 , and A 40 are each independently selected from H and a monovalent organic group with the proviso that A 40 and A 44 are not mesityl or methylphenol, and A 42 is selected from H, a monovalent organic group, a halogen, and an inorganic group; or
General formula (vii) is
where subscript e is an integer from 0 to 4, each A 53 is independently selected from a monovalent organic group, a halogen, and an inorganic group, with the proviso that when e>1, then A 53 may form a ring structure with another A 53 , and A 52 and A 51 are each independently selected from H, monovalent organic group, a halogen, and an inorganic group, with the proviso that A 51 and A 52 may combine to form a ring structure; or General formula (xiii) is
where A 111 is selected from H, monovalent organic group, a halogen and an inorganic group, and A 102 is selected from H and a monovalent organic group; or
General formula (xvi) is
where subscript t is an integer from 0 to 3, subscript u is an integer from 1 to 3, and each A 141 and each A 142 are independently selected from a monovalent organic group, a halogen, and an inorganic group; or
General formula (xvii) is
where subscript w is an integer from 0 to 4, each A 151 is independently selected from a monovalent organic group, a halogen and an inorganic group, and A 152 and A 153 are each independently selected from a monovalent organic group, a halogen and an inorganic group; or
General formula (xviii) is
where subscript x is an integer from 0 to 4, each A 161 is independently selected from a monovalent organic group, a halogen, and an inorganic group, and A 162 , A 163 , and A 164 are each independently a monovalent organic group;
General formula (xix) is
where subscript aa is an integer from 0 to 4, subscript bb is an integer from 0 to 4, each A 171 is independently selected from a monovalent organic group, a halogen and an inorganic group, each A 172 is independently selected from a monovalent organic group, a halogen and an inorganic group, and A 173 and A 174 are each independently a monovalent organic group; or
General formula (xx) is
where subscript cc is an integer from 0 to 4, each A 181 is independently selected from a monovalent organic group, a halogen, and an inorganic group, and A 182 is a monovalent organic group; or
General formula (xxi) is
where subscript dd is an integer from 0 to 4, each A 191 is independently selected from a monovalent organic group, a halogen, and an inorganic group, A 192 , A 194 , and A 195 are each independently a monovalent organic group, and A 193 is selected from a monovalent organic group, H, a halogen, and an inorganic group; or
General formula (xxii) is
where subscript ee is an integer from 0 to 4, each A 201 is independently selected from a monovalent organic group, a halogen, and an inorganic group, and A 202 is selected from a monovalent organic group, H, a halogen, and an inorganic group; or
thereby making a reaction product comprising a Fe-ligand complex.
12. The method of claim 11 , where one of conditions (a) to (c) is satisfied, where:
Condition (a) is each A is an ester group; or
Condition (b) is each A is stearate; or
Condition (c) is each A is acetate.
13. The method of claim 11 , where one of conditions (A) and (B) is satisfied, where:
Condition (A) is the ligand is selected from the group consisting of ligands 5, 10, 23, 32, 33, 37, 41, 42, 43, 44, 50, 56, 58, 66, 68, 76, 78, 80, 81, 83, 100, 101, 103, 105, 108, 109, 110, 113, 114, 115, 116, 118, 122, 123, 125, 131, 141, 154, 168, 169, 171, 172, 173, 174, 175, 177, 178, 179, 188, 189, 192, and 208; or
Condition (B) is the ligand is selected from the group consisting of ligands 234, 239, 240, 250, or 285.
14. The method of claim 11 , where one of conditions (I) to (V) is satisfied, where
Condition (I) is that each A is an ester group, and the ligand is one of 5, 10, 23, 32, 33, 37, 41, 42, 43, 44, 50, 56, 58, 66, 68, 76, 78, 80, 81, 83, 100, 101, 103, 105, 108, 109, 110, 113, 114, 115, 116, 118, 122, 123, 125, 131, 141, 154, 168, 169, 171, 172, 173, 174, 175, 177, 178, 179, 188, 189, 192, 208, 234, 239, 240, 250, or 285; or
Condition (II) is that each A is a stearate group, and the ligand is one of 5, 10, 23, 32, 33, 37, 41, 42, 43, 44, 50, 56, 58, 66, 68, 76, 78, 80, 81, 83, 100, 101, 103, 105, 108, 109, 110, 113, 114, 115, 116, 118, 122, 123, 125, 131, 141, 154, 168, 169, 171, 172, 173, 174, 175, 177, 178, 179, 188, 189, 192, or 208 in Table 1; or
Condition (III) is that each A is an acetate group and the ligand is one of 227, 230, 231, 233, 234, 239, 240, 250, or 285; or
Condition (IV) is that each A is a stearate group, and the ligand has one of general formulae (ii), (iii), (iv), (v), (vi), (vii), (xix), (xx), (xxi), or (xxii); or
Condition (V) is that each A is an acetate group, and the ligand has one of general formulae (xiii), (xvi), (xvii), or (xviii).
15. The method of claim 11 , further comprising heating the Fe precursor and the ligand.
16. The method of claim 11 , further comprising removing a by-product from the reaction product to yield the Fe-ligand complex free of the by-product.
17. A reaction product prepared by the method of claim 11 .
18. The reaction product of claim 17 , where the reaction product comprises:
a) a Fe-ligand complex, and
b) a by-product from the reaction of the Fe precursor and the ligand, or from a side reaction therein.
19. A reaction product prepared by the method of claim 16 .