Infusion of cyclic olefin resins into porous materials

• US 20030186035A1
• Filed: 08/30/2002
• Published: 10/02/2003
• Est. Priority Date: 08/30/2001
• Status: Abandoned Application

• Current Assignee: Materia Incorporated (Exxon Mobil Corporation)
• Original Assignee: Materia Incorporated (Exxon Mobil Corporation)
• Inventors: Cruce, Christopher J., Giardello, Michael A., Filice, Gary W., Trimmer, Mark S., Stephen, Anthony R.
• Application Number:
  US10/233,066
• Publication Number:
  US 20030186035A1
• Time in Patent Office: Days
• US Class Current: 428/292.4
• CPC Class Codes: C04B 2111/27 Water resistance, i.e. waterproof or water-repellent materials
• CPC Class Codes: C04B 28/02 containing hydraulic cements other than calcium sulfates
• CPC Class Codes: C04B 41/009 characterised by the material treated
• CPC Class Codes: C04B 41/4521 application under increased pressure
• CPC Class Codes: C04B 41/4857 Other macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C04B 41/63 Macromolecular compounds
• CPC Class Codes: C08J 2423/00 Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
• CPC Class Codes: C08J 9/42 with macromolecular compounds
• CPC Class Codes: C08K 3/01 characterized by their specific function
• CPC Class Codes: C08K 5/098 Metal salts of carboxylic acids
• CPC Class Codes: C08K 5/5425 containing at least one C=C bond
• CPC Class Codes: C08L 23/02 not modified by chemical after-treatment
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 2666/06 Homopolymers or copolymers of unsaturated hydrocarbons; Derivatives thereof
• CPC Class Codes: C08L 2666/22 Macromolecular compounds not provided for in C08L2666/16 - C08L2666/20
• CPC Class Codes: C08L 2666/26 Natural polymers, natural resins or derivatives thereof according to C08L1/00 - C08L5/00, C08L89/00, C08L93/00, C08L97/00 or C08L99/00
• 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
• CPC Class Codes: C08L 79/02 Polyamines
• CPC Class Codes: C08L 97/02 Lignocellulosic material, e.g. wood, straw or bagasse manufacture of articles made from lignocellulosic material by dry processes B27N
• CPC Class Codes: Y10T 428/249925 Fiber-containing wood product [e.g., hardboard, lumber, or wood board, etc.]

Abstract

The present invention relates to novel compositions comprising porous materials infused with polymers obtained from metathesis reactions, for example ROMP derived polymers and ADMET derived polymers. The invention further relates to cyclic olefin monomer formulations, including ruthenium or osmium carbene metathesis catalysts, useful for the infusion of porous materials. Also disclosed are methods for preparing the porous materials infused with cyclic olefin resin formulations.

Claims

1. A composition comprising a porous material infused with a metathesis-derived polyolefin.

2. The composition of claim 1, further comprising a coupling agent.

3. The composition of claim 2, wherein the coupling agent is selected from the group consisting of organotitanates, organozirconates, and silanes.

4. The composition of claim 1 wherein the porous material is selected from the group consisting of a non-organic material and an organic material.

5. The composition of claim 1, wherein the porous material is selected from the group consisting of wood, cement, concrete, open-cell and reticulated foams and sponges, papers, cardboards, felts, ropes and braids of natural or synthetic fibers, sintered materials, unglazed porous ceramics, compacted free standing metal powder objects, porous concrete aggregates, wood, wood products, and cellulosic materials.

6. The composition of claim 1, wherein the metathesis-derived polyolefin is selected from the group consisting of a ROMP polymer and an ADMET polymer.

7. The composition of claim 1, wherein the metathesis-derived polyolefin is prepared from one or more olefin monomers selected from the group consisting of norbornenes, cyclopropenes, cyclobutenes, benzocyclobutenes, cyclopentenes, cyclopentadiene oligomers, cyclohexenes, cycloheptenes, cyclooctenes, cyclooctadienes, norbornadienes, [2.2.1]bicycloheptenes, and [2.2.2]bicyclooctene, cyclohexenylnorbornenes, and norbornene dicarboxylic anhydrides.

8. The composition of claim 1, wherein the metathesis-derived polyolefin is polydicyclopentadiene.

9. The composition of claim 1, wherein the metathesis-derived polyolefin is polymerized using a ruthenium or osmium metal carbene catalyst.

10. The composition of claim 1, wherein the metathesis-derived polyolefin is polymerized using a catalyst selected from the group consisting of a catalyst of the formula:

11. A method for preparing a polyolefin-infused porous material comprising:

mixing an olefin monomer resin formulation with a metathesis catalyst to form a catalyzed resin formulation, infusing the mixture into the porous material, and curing the catalyzed resin formulation within said porous material.

12. The method of claim 11 wherein the porous material is selected from the group consisting of wood, cement, concrete, open-cell and reticulated foams and sponges, papers, cardboards, felts, ropes or braids of natural or synthetic fibers, and sintered materials.

13. The method of claim 11, wherein the olefin monomer resin formulation comprises an olefin monomer selected from the group consisting of norbornenes, cyclopropenes, cyclobutenes, benzocyclobutenes, cyclopentenes, cyclopentadiene oligomers, cyclohexenes, cycloheptenes, cyclooctenes, cyclooctadienes, norbornadienes, [2.2.1]bicycloheptenes, and [2.2.2]bicyclooctene, cyclohexenylnorbornenes, and norbornene dicarboxylic anhydrides.

14. The method of claim 11, wherein the olefin monomer resin formulation comprises dicyclopentadiene.

15. The method of claim 11, wherein the olefin monomer resin formulation includes a coupling agent.

16. The method of claim 11, wherein the coupling agent is selected from the group consisting of organotitanates, organozirconates, and silanes.

17. The method of claim 11, wherein the metathesis catalyst is a ruthenium or osmium metal carbene complex.

18. The method of claim 11, wherein the wherein the metathesis catalyst is selected from the group consisting of a catalyst of the formula:

19. A method for preparing a polyolefin-infused wood object comprising:

spraying the wood object with a cleaning and wetting high-pressure water spray;

drying the object, wherein the drying is performed by heat and vacuum;

infusing the object with a mixture of an olefin monomer resin formulation and a metathesis catalyst under pressure;

curing the catalyzed resin formulation within the wood object;

and post-curing the polyolefin-infused wood object.

20. An article of manufacture comprising a porous material infused with a metathesis-derived polyolefin.

21. The article of manufacture of claim 20, wherein the article is selected from the group consisting of golf tees, golf clubs, weighted golf club heads, golf club shafts, golf club gradient shafts, basketball backboards, tennis rackets, squash rackets, racquetball rackets, badminton rackets, snow boards, surfboards, boogie board, skis, backboards, sleds, toboggans, baseball bats, cricket bats, hockey sticks, pool cues, archery bows, archery arrows, rifle butts, polo mallets, croquet mallets, tent stakes, piers, docks, posts, decking, hulls, oars, propellers, rudders, keels, masts, boat fascia, kayaks, canoes, ferro-cement boats, hand-tool handles, knife handles, ladders, wood flooring panels, deck lumber, treated concrete or cinder blocks, door and window frames, office furniture, concrete bridge decks, parking structure ramps, post-tensional beams and slabs, treated concrete pipes and channel liners for aggressive and acidic fluids, sewer pipes, containment structures, pavers, stone consolidation, plaster or concrete ornamental objects, and pre-cast concrete objects.

22. The article of manufacture of claim 20, wherein the article is a baseball bat.