COMPOSITION AND ASSOCIATED METHOD

• US 20090062442A1
• Filed: 09/04/2007
• Published: 03/05/2009
• Est. Priority Date: 09/04/2007
• Status: Active Grant

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: Lin, Wendy Wen-Ling, Wei, Xiaolan
• Granted Patent: US 8,039,544 B2
• Time in Patent Office: Days
• US Class Current: 524/198
• CPC Class Codes: C08G 2261/3324 derived from norbornene
• CPC Class Codes: C08G 2261/3325 derived from other polycyclic systems
• CPC Class Codes: C08G 2261/3342 derived from cycloolefins containing heteroatoms
• CPC Class Codes: C08G 2261/418 Ring opening metathesis polymerisation [ROMP]
• CPC Class Codes: C08G 59/08 from phenol-aldehyde condensates
• CPC Class Codes: C08L 65/00 Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain C08L7/00 - C08L57/00, C08L61/00 take precedence; Compositions of derivatives of such polymers

Abstract

A composition includes a first cycloolefin substituted with at least one epoxy group and an aromatic amine. The composition is capable of bonding to a filler having a corresponding binding site. The composition is compatible with a metathesis catalyst capable of catalyzing a ring-opening metathesis polymerization reaction when contacted to the first cycloolefin. An associated method is also provided.

Claims

1. A composition, comprising:

a first cycloolefin substituted with at least one epoxy group; and

an aromatic amine;

wherein the composition is capable of bonding to a filler having a corresponding binding site and the composition is compatible with a metathesis catalyst capable of catalyzing a ring-opening metathesis polymerization reaction when contacted to the first cycloolefin.

2. The composition as defined in claim 1, wherein the metathesis catalyst comprises a structure having a formula (I)

3. The composition as defined in claim 1, wherein the first cycloolefin comprises a structure having a formula (V), (VI), or (VII)

4. The composition as defined in claim 1, wherein the aromatic amine comprises at least one primary amine group.

5. The composition as defined in claim 1, wherein the aromatic amine comprises at least two primary amine groups.

6. The composition as defined in claim 1, wherein the aromatic amine comprises a structure having a formula (XXII)

7. The composition as defined in claim 6, wherein R¹⁷ and R¹⁸ are independently at each occurrence an aliphatic radical.

8. The composition as defined in claim 6, wherein R¹⁹ is a bond, an oxygen atom, or C(R²⁰)₂.

9. The composition as defined in claim 1, wherein a molar ratio of the cycloolefin to the aromatic amine is in a range of from about 1:

9 to about 9;

1.

10. The composition as defined in claim 1, wherein the coupling agent composition is capable of bonding to the corresponding binding sites on the filler by covalent bond formation.

11. The composition as defined in claim 1, wherein the binding site comprises one or more of an epoxy group, a hydroxyl group, an amine group, an amide group, a nitrate group, an isocyanate group, a carbamate groups, a urea group, a carbonyl group, or a carboxylic group.

12. The composition as defined in claim 1, wherein the binding site comprises one or more of a silanol group, a siloxane group, or an acrylate group.

13. The composition as defined in claim 1, wherein the filler comprises a sizing composition comprising one or more of epoxy, urethane, polyvinyl alcohol, vinyl ester, polyester, or fatty acid ester.

14. The composition as defined in claim 1, comprising the metathesis catalyst.

15. A composition, comprising:

the composition as defined in claim 1; and

the filler having binding sites.

16. The composition as defined in claim 15, 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.

17. The composition as defined in claim 15, 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.

18. The composition as defined in claim 15, wherein the filler comprises a fibrous material.

19. The composition as defined in claim 18, wherein the fibrous material comprises a carbon fiber or a polymer fiber.

20. The composition as defined in claim 18, wherein the fibrous material comprises a glass fiber or a ceramic fiber.

21. The composition as defined in claim 18, wherein the fibrous material is configured as at least one of a yarn, a mat, a fabric, a woven roving, or a continuous filament.

22. The composition as defined in claim 18, wherein the fibrous material comprises a plurality of fibers having an average diameter in a range of from about 1 nanometer to about 1000 micrometers.

23. The composition as defined in claim 15, wherein the composition is bonded to the corresponding binding site of the filler.

24. A composition, comprising a reaction product of:

a first cycloolefin substituted with at least one epoxy group; and

an aromatic amine;

wherein the reaction product is bound to a corresponding binding site on a filler and the reaction product is compatible with a metathesis catalyst capable of catalyzing a ring-opening metathesis polymerization reaction when contacted to the first cycloolefin.

25. The composition as defined in claim 24, wherein the reaction product is bound to the filler by epoxy-amine bond formation

26. A method, comprising:

contacting a filler and coupling agent composition comprising an aromatic amine and a first cycloolefin that is substituted with at least one epoxy group,

wherein the coupling agent composition is capable of bonding to a binding site on the filler and the coupling agent composition is compatible with a metathesis catalyst capable of catalyzing a ring-opening metathesis polymerization reaction when contacted to the first cycloolefin.

27. The method as defined in claim 26, comprising contacting the first cycloolefin with the aromatic amine at a temperature in a range of from about 100 degrees Celsius to about 175 degrees Celsius.

28. The method as defined in claim 26, comprising contacting the first cycloolefin with the aromatic amine at a temperature in a range of from about 175 degrees Celsius to about 250 degrees Celsius.

29. The method as defined in claim 26, wherein contacting comprises binding the coupling agent composition to the filler binding site.

30. The method as defined in claim 26, comprising binding the coupling agent composition to the filler by epoxy-amine bond formation.