Composition, article, and associated method
A composition includes a coupling agent composition and a polymer precursor. The coupling agent includes a first cycloolefin substituted with at least one anhydride group and the coupling agent is capable of bonding to a filler having a corresponding binding site. The polymer precursor includes a second cycloolefin. An associated article and a method are also provided.
1. A composition, comprising:
a coupling agent composition comprising a first cycloolefin substituted with at least one anhydride group;
a filler having a corresponding binding site; and
a polymer precursor comprising a second cycloolefin;
wherein the coupling agent composition is capable of bonding to the filler having the corresponding binding site.
2. The composition as defined in claim 1 , wherein the first cycloolefin comprises a structure having a formula (I), (II), or (III)
wherein “w” is 0, 1, 2 or 3, “x” is 0, 1, or 2, “y” is 1 or 2; “z” is 1, 2, 3, or 4;
R 1 and R 3 are independently at each occurrence a halogen atom, an aliphatic radical, a cycloaliphatic radical, an aromatic radical, an alkoxy group, a hydroxy group, an ether group, an aldehyde group, an ester group, a ketone group, a thiol group, a disulfide group, an amine group, an amide group, a quaternary amine group, an imine group, an isocyanate group, a carboxyl group, a silanyl group, a phosphanyl group, a sulfate group, a sulfonate group, a nitro group, or a divalent bond linking two carbon atoms;
R 2 comprises at least one anhydride group;
R 4 is an aliphatic cyclic ring, a heterocycle, or an aromatic group; and
Z is C(R 5 ) 2 , C═C(R 5 ) 2 , Si(R 5 ) 2 , O, S, N—R 5 , P—R 5 , B—R 5 , or As—R 5 , wherein R 5 is independently at each occurrence hydrogen, an aliphatic radical, a cycloaliphatic radical, or an aromatic radical.
3. The composition as defined in claim 1 , wherein the second cycloolefin comprises a structure having a formula (XIX):
wherein “v” is 1, 2, 3, 4, 5, or 6;
R 8 is independently at each occurrence a halogen atom, an aliphatic radical, a cycloaliphatic radical, an aromatic radical, an alkoxy group, a hydroxy group, an ether group, an aldehyde group, an ester group, a ketone group, a thiol group, a disulfide group, an amine group, an amide group, a quaternary amine group, an imine group, an isocyanate group, a carboxyl group, a silanyl group, a phosphanyl group, a sulfate group, a sulfonate group, a nitro group, or two or more R 8 together form a cycloaliphatic radical, an aromatic radical, an imide group, a cycloolefin group, or a divalent bond linking two carbon atoms; and
Y is C(R 9 ) 2 , C═C(R 9 ) 2 , Si(R 9 ) 2 , O, S, NR 9 , PR 9 , BR 9 , or AsR 9 , wherein R 9 is independently at each occurrence hydrogen, an aliphatic radical, a cycloaliphatic radical, or an aromatic radical.
4. The composition as defined in claim 1 , wherein the second cycloolefin comprises one or more of dicyclopentadiene, norbornene, oxanorbornene, norbornadiene, cyclooctadiene, cyclooctene, cyclotetraene, cyclodecene, cyclododecene, or a derivative thereof.
5. The composition as defined in claim 1 , further comprising a metathesis catalyst capable of catalyzing a ring-opening metathesis polymerization reaction when contacted to the first cycloolefin or the second cycloolefin.
6. The composition as defined in claim 5 , wherein the metathesis catalyst comprises a structure having a formula (XXII):
wherein “a” and “b” are independently integers from 1 to 3, with the proviso that “a+b” is less than or equal to 5;
M is ruthenium or osmium;
X is independently at each occurrence an anionic ligand;
L is independently at each occurrence a neutral electron donor ligand;
R 12 is hydrogen, an aliphatic radical, a cycloaliphatic radical, or an aromatic radical; and
R 13 is an aliphatic radical, a cycloaliphatic radical, an aromatic radical, or S—R 14 ; or two or more of X, L, R 12 and R 13 independently form a cyclic group; and
R 14 is an aliphatic radical, a cycloaliphatic radical, or an aromatic radical.
7. The composition as defined in claim 6 , wherein the coupling agent composition is compatible with the metathesis catalyst.
8. The composition as defined in claim 1 , wherein the coupling agent composition is present in an amount in a range of from about 0.5 weight percent to about 50 weight percent of the total weight of the composition.
9. The composition as defined in claim 1 , wherein the coupling agent composition is capable of bonding to the filler-binding site by covalent bond formation.
10. The composition as defined in claim 1 , wherein the filler comprises one or more material selected from the group consisting of siliceous materials, carbonaceous materials, metal hydrates, metal oxides, metal borides, and metal nitrides.
11. The composition as defined in claim 1 , wherein the filler comprises a plurality of particles having a shape of a sphere, a rod, a tube, a flake, a plate, or a whisker, or the plurality comprises a combination of two or more of the foregoing shapes.
12. The composition as defined in claim 1 , wherein the filler comprises a fibrous material.
13. The composition as defined in claim 12 , wherein the fibrous material comprises a carbon fiber or a polymer fiber.
14. The composition as defined in claim 12 , wherein the fibrous material comprises a glass fiber or a ceramic fiber.
15. The composition as defined in claim 1 , wherein the filler is present in an amount in a range of from about 20 weight percent to 80 weight percent of the composition.
16. An article, comprising a reaction product of:
a coupling agent composition comprising a first cycloolefin substituted with at least one anhydride group;
a polymer precursor comprising a second cycloolefin;
a metathesis catalyst capable of catalyzing a ring-opening metathesis polymerization reaction when contacted to the first cycloolefin or to the second cycloolefin; and
a filler having binding sites capable of reacting with the coupling agent.
17. A cured composite structure comprising the article of claim 16 .
18. A method, comprising:
contacting a coupling agent composition with a polymer precursor to form a curable composition; and
contacting the curable composition with a filler having binding sites to which the coupling agent composition can bond,
wherein the coupling agent composition comprises a first cycloolefin substituted with at least one anhydride group and the polymer precursor comprises a second cycloolefin.
19. The method as defined in claim 18 , further comprising contacting the curable composition with a metathesis catalyst.
20. The method as defined in claim 18 , further comprising curing the curable composition to form an article.
21. The method as defined in claim 18 , further comprising covalently bonding the first cycloolefin to the filler.