CA2628710A1 - Nanocomposite compositions and processes for making the same - Google Patents

Nanocomposite compositions and processes for making the same Download PDF

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Publication number
CA2628710A1
CA2628710A1 CA002628710A CA2628710A CA2628710A1 CA 2628710 A1 CA2628710 A1 CA 2628710A1 CA 002628710 A CA002628710 A CA 002628710A CA 2628710 A CA2628710 A CA 2628710A CA 2628710 A1 CA2628710 A1 CA 2628710A1
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Prior art keywords
clay
nanocomposite composition
rubber
acid
functionalized interpolymer
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CA002628710A
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French (fr)
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CA2628710C (en
Inventor
Caiguo Gong
Anthony Jay Dias
Weiqing Weng
Ramanan Krishnamoorti
Carmen Neagu
Molly Westermann Johnston
Beverly Jean Poole
Kriss Randall Karp
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ExxonMobil Chemical Patents Inc
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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B60VEHICLES IN GENERAL
    • B60CVEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B60C1/0008Compositions of the inner liner
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B82NANOTECHNOLOGY
    • B82YSPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00Nanotechnology for materials or surface science, e.g. nanocomposites
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/005Reinforced macromolecular compounds with nanosized materials, e.g. nanoparticles, nanofibres, nanotubes, nanowires, nanorods or nanolayered materials
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2323/00Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2323/02Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
    • C08J2323/18Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C08J2323/20Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • C08J2323/22Copolymers of isobutene; butyl rubber
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2325/00Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
    • C08J2325/18Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00Use of pretreated ingredients
    • C08K9/08Ingredients agglomerated by treatment with a binding agent
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L21/00Compositions of unspecified rubbers

Abstract

The invention provides for processes for preparing a nanocomposite compositions including the steps of: contacting a multifunctional intercalant including a cationic moiety separated from an anionic moiety by at least 1 carbon, with a clay at a temperature and for a period of time sufficient to produce an at least partially intercalated clay; and contacting the at least partially intercalated clay with a functionalized interpolymer including one or more functional groups, at a temperature, and for a period of time sufficient to produce the nanocomposite compositions. Cured nanocomposite compositions, and articles including such nanocomposite compositions are also provided.

Claims (81)

1. A process for preparing a nanocomposite composition, comprising the steps of:

(a) contacting a multifunctional intercalant comprising a cationic moiety separated from an anionic moiety by at least 1 carbon, with a clay at a temperature and for a period of time sufficient to produce an at least partially intercalated clay; and (b) contacting the at least partially intercalated clay with a functionalized interpolymer comprising one or more functional groups, at a temperature, and for a period of time sufficient to produce the nanocomposite composition, wherein the functionalized interpolymer comprises a random elastomeric copolymer comprising C2-C8 olefin monomer, alkylstyrene monomer, and functionalized alkylstyrene monomer.
2. The process of claim 1, wherein the C2-C8 olefin monomer comprises ethylene, a C4 to C7 isomonoolefin, a C3-C6 alpha olefin, or a combination thereof.
3. The process of claim 1, wherein the C4 to C7 isomonoolefin comprises isobutylene.
4. The process of claim 1, wherein at least 80 wt% of the alkylstyrene monomer is a para-alkylstyrene monomer.
5. The process of claim 1, wherein the functionalized alkylstyrene monomer comprises a benzylic functional group selected from the group consisting of: halogen, carboxylic acid; carboxy salt; carboxy esters, amide, imide, hydroxy; alkoxide; phenoxide; thiolate; thioether; xanthate; cyanide;
cyanate; isocyanide, amino, and a combination thereof.
6. The process of claim 1, wherein the functionalized alkylstyrene monomer comprises para-bromomethyl styrene.
7. The process of claim 1, wherein the alkylstyrene monomer comprises para-methylstyrene.
8. The process of any one of claims 1 to 7, wherein the functionalized interpolymer comprises 3 to 15 wt% para-methyl styrene.
9. The process of any one of claims 1 to 8, wherein the functionalized interpolymer comprises up to 15 mol% functionalized alkylstyrene monomer.
10. The process of any one of claims 1 to 9, wherein the functionalized interpolymer comprises 0.1 to 10 mol% para-bromomethyl styrene monomer.
11. The process of any one of claims 1 to 10, wherein at least 95 wt% of the functionalized interpolymer has a para-alkylstyrene content within 10% of the average para-alkylstyrene content of the functionalized interpolymer.
12. The process of any one of claims 1 to 11, wherein the functionalized interpolymer comprises a halogenated rubber component selected from the group consisting of: brominated butyl rubber, chlorinated butyl rubber, star-branched polyisobutylene rubber, star-branched brominated butyl rubber; isobutylene/meta-bromomethylstyrene rubber, isobutylene/para-bromomethylstyrene rubber, isobutylene/chloromethylstyrene rubber, halogenated isobutylene cyclopentadiene rubber, isobutylene/para-chloromethylstyrene rubber, polychloroprene rubber, and combinations thereof.
13. The process of any one of claims 1 to 12, wherein the clay comprises a natural phyllosilicate clay , a synthetic phyllosilicate clay, or a combination thereof.
14. The process of any one of claims 1 to 13, wherein the clay comprises a smectic clay.
15. The process of any one of claims 1 to 14, wherein the clay is selected from the group consisting of montmorillonite, nontronite, beidellite, volkonskoite, laponite, hectorite, saponite, sauconite, magadite, kenyaite, stevensite, vermiculite, halloysite, aluminate oxides, hydrotalcite, and combinations thereof.
16. The process of any one of claims 1 to 15, wherein the clay comprises particles having a plurality of silicate platelets of a thickness of 0.8-1.2 nanometers, and exchangeable cations selected from the group consisting of Na+; Ca+2, K+ and Mg+2, present at an interlayer surface of the silicate platelets.
17. The process of any one of claims 1 to 16, wherein the nanocomposite composition comprises 0.5 to 10 wt% clay.
18. The process of any one of claims 1 to 17, wherein the multifunctional intercalant is represented by the formula:
(CM)n-R1-(AM)m, wherein:
CM is a cationic moiety;
R1 comprises at least 1 carbon atom;
AM is an anionic moiety; and n and m are each greater than or equal to 1.
19. The process of claim 18, wherein the cationic moiety is an ammonium ion, a phosphonium ion, or a cation derived from one or more of a phosphine, an alkyl sulfide, an aryl sulfide, or a thiol.
20. The process 18, wherein the multifunctional intercalant is represented by the structure R2R3N-R1-AM, or R2R3R4N+-R1-AM, wherein R1 is a C1 to C50 hydrocarbyl, substituted hydrocarbyl, halocarbyl, or substituted halocarbyl; and wherein R2, R3, and R4 when present, are each independently, hydrogen, C1 to C30 hydrocarbyls, substituted hydrocarbyls, halocarbyls, or substituted halocarbyls.
21. The process of claim 20, wherein R2 and R3 are methyl or ethyl, R4 is hydrogen, and R1 is a C8-C12 aliphatic alkyl or substituted aliphatic alkyl.
22. The process of claim 20, wherein R2 and R3 are methyl or ethyl, R4 is hydrogen, and R1 is a C6-C10 aromatic group or a substituted aromatic group.
23. The process of any one of claims 18 to 22, wherein R1 comprises at least 4 carbon atoms.
24. The process of any one of claims 18 to 23, wherein R1 comprises at least 11 carbon atoms.
25. The process of any one of claims 18 to 24, wherein R1 comprises 10 to 12 carbon atoms.
26. The process of any one of claims 18 to 25, wherein R1 is a C14 to C20 alkyl or alkene.
27. The process of any one of claims 18 to 26, wherein the anionic moiety is a carboxylic acid; a carboxy salt; a carboxy ester, an amide, an imide; a hydroxy; an alkoxide; a phenoxide; a thiolate; a thioether; a xanthate; a cyanide; a cyanate; a phosphate; a phosphite; a sulfate; a sulfite; or a combination thereof.
28. The process of any one of claims 18 to 27, wherein the anionic moiety is a carboxylate anion.
29. The process of any one of claims 1 to 28, wherein the multifunctional intercalant is selected from the group consisting of 12-aminododecanoic acid, N-substituted 12-aminododecanoic acid, N,N-disubstituted 12-aminododecanoic acid, and N,N,N-trisubstituted 12-aminododecanoic acid, wherein the N-substituents are C1-C12 alkyl groups, alanine, arginine, asparagines, aspartic acid, cysteine, glutamine, glutamic acid, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, aspartic acid, and glutamic acid.
30. The process of any one of claims 1 to 29, wherein the multifunctional intercalant is epsilon-caprolactam, aminobenzoic acid, or a C1-C10 alkyl substituted aminobenzoic acid.
31. The process of any one of claims 1 to 30, wherein the multifunctional intercalant is dimethylaminobenzoic acid.
32. The process of any one of claims 1 to 31, wherein the clay is further contacted with an additional intercalant selected from the group consisting of:
polysilanes of the structure --Si(R5)2R6 where R5 is the same or different at each occurrence and is selected from alkyl, alkoxy or oxysilane and R6 is an organic radical;

primary, secondary, or tertiary amines; primary, secondary, or tertiary phosphines; alkyl sulfides; aryl sulfides; alkyl thiols; aryl thiols: and their polyfunctional analogs.
33. The process of any one of claims 1 to 32, wherein the clay is further contacted with an additional intercalant selected from the group consisting of:
N,N-dimethyl-octadecylamine, N,N-dioctadecyl-methylamine, dihydrogenated tallowalkyl-methylamine, amine-terminated polytetrahydrofuran, hexamethylene sodium thiosulfate, and a combination thereof.
34. The process of any one of claims 1 to 33, wherein the multifunctional intercalant is present in the nanocomposite composition at 0.1 to 20 phr.
35. The process of any one of claims 1 to 34, wherein the at least partially intercalated clay comprises layered platelets spaced at a distance of greater than 0.4 nm.
36. The process of any one of claims 1 to 35, further comprising the step of contacting the multifunctional intercalant with the clay in the presence of an intercalation modifier, and/or the step of contacting the at least partially intercalated clay with the functionalized interpolymer in the presence of an intercalation modifier, wherein the intercalation modifier is a surfactant, a block copolymer, a wetting agent, an emulsifying agent, or a combination thereof, and wherein the intercalation modifier is present in the nanocomposite composition at greater than or equal to 0.1 wt%.
37. The process of claim 36, wherein the intercalation modifier comprises a non-ionic surfactant, an anionic surfactant, an amphoteric surfactant, a cationic surfactant, or a combination thereof.
38. The process of claim 36, wherein the intercalation modifier comprises a cationic surfactant selected from the group consisting of:
polyoxyethylene and/or polyoxypropylene tertiary C1-C18 alkylamines, C1-C18 substituted tertiary alkylamines, C1-C18 substituted tertiary alkenylamines, ethoxylated and/or propoxylated fatty amines, C1-C18 alkyl-substituted fatty amines, polyoxyethylene and/or polyoxypropylene C1-C18 alkyletheramines, polyoxyethylene and/or polyoxypropylene cocoamines, polyoxyethylene and/or polyoxypropylene tallowamines, polyoxyethylene and/or polyoxypropylene quaternary tallowamines, distearyldimethylammonium chloride or bromide, N-dodecylpyridine chloride or bromide, dimethyldioctadecyl ammonium bromide, and polyoxypropylene ethoxytrimethylammonium chloride or bromide.
39. The process of claim 36, wherein the intercalation modifier comprises a surface active agent selected from the group consisting of:
polyacrylic acid salts, lignosulphonic acid salts, phenolsulphonic acids, naphthalenesulphonic acids, alkylphenol ethoxylates, arylphenol ethoxylates, sulphonosuccinic acid ester salts, alkyl taurates, phosphoric esters of alcohols, and derivatives having sulphate, sulphonate or phosphate groups of the above surface active agents.
40. The process of any one of claims 1 to 39, further comprising the step of adding one or more additives, wherein the additives comprise a secondary rubber component, a filler, a curative system, a dye, a pigment, an antioxidant, a heat stabilizer, a light stabilizer, a plasticizer, an oil, or a combination thereof.
41. The process of claim 40, wherein the secondary rubber component comprises natural rubber, polyisoprene rubber, poly(styrene-co-butadiene) rubber, polybutadiene rubber, poly(isoprene-co-butadiene) rubber, styrene-isoprene-butadiene rubber, ethylene-propylene rubber, ethylene-propylene-diene rubber, polysulfide rubber, nitrile rubber, propylene oxide rubber polymers, star-branched butyl rubber, and mixtures thereof.
42. The process of any one of claims 40 or 41, wherein the secondary rubber component is present in the nanocomposite composition at 1 to 90 phr.
43. The process of any one of claims 1 to 42, further comprising adding a filler comprising calcium carbonate, clay, mica, silica, a silicate, talc, titanium dioxide, carbon black, or a combination thereof.
44. The process of any one of claims 1 to 43, wherein the filler is carbon black or a modified carbon black.
45. The process of any one of claims 1 to 44, wherein the filler is semi-reinforcing grade carbon black present at a level of from 10 to 150 phr in the nanocomposite composition.
46. The process of claim 40, wherein the curative system comprises a polyfunctional curatives described by the formula Z-R7-Z', wherein R7 is one of a C1 to C15 alkyl, a C2 to C15 alkenyl, or a C6 to C12 cyclic aromatic moiety, substituted or unsubstituted; and Z and Z' are the same or different and are one of a thiosulfate group, a mercapto group, an aldehyde group, a carboxylic acid group, a peroxide group, an alkenyl group, or a combination thereof.
47. The process of claim 40, wherein the curative system comprises hexamethylene bis(sodium thiosulfate), hexamethylene bis(cinnamaldehyde), or a combination thereof.
48. The process of claim 46, wherein the polyfunctional curative system is present in the nanocomposite composition at 0.1 to 8 phr.
49. The process of claim 40, wherein the curative system comprises di-ortho-tolylguanidine salt of dicatechol borate, m-phenylene bis maleimide, 2, 4, 6-trimercapto-5 triazine, zinc diethyl dithiocarbamate, dipenta-methylene thiuram hexasulfide, alkylated phenol disulfide, phenol formaldehyde resin, brominated alkyl phenol formaldehyde resin, diphenyl phenylene diamine, salicyclic acid, wood rosin, tetramethyl thiuram disulfide in combination with sulfur, stearic acid, diphenyl guanidine, tetramethylthiuram disulfide, 4,4'-dithiodimorpholine, tetrabutylthiuram disulfide, 2,2'-benzothiazyl, N-tertiarybutyl-2-benzothiazole sulfenamide, N-oxydiethylene thiocarbamyl-N-oxydiethylene sulfonamide, zinc 2-ethyl hexanoate, N,N'-diethyl thiourea, or a combination thereof.
50. The process of claim 40, wherein the curative system is added to the nanocomposite composition in an amount equal to 0.2 to 15 phr.
51. The process of any one of claims 1 to 50, wherein the multifunctional intercalant is contacted with the clay at a temperature of 20°C to 120°C, for a period of time of 1 minute to 24 hours.
52. The process of any one of claims 1 to 51, wherein the intercalated clay is contacted with the functional interpolymer at a temperature of 40°C to 140°C, for a period of time of 1 minute to 24 hours.
53. The process of any one of claims 1 to 52, wherein the multifunctional intercalant is contacted with, the clay in the presence of an acid such that the pH of the mixture of the multifunctional intercalant and the clay is below 7.
54. The process of claim 53, wherein the acid is selected from the group consisting of HC1, HBr, HI, HF, phosphoric acid, phosphorous acid, sulfuric acid, or a combination thereof.
55. The process of any one of claims 1 to 54, wherein the intercalated clay is contacted with the functional interpolymer in the presence of a base such that the pH of the mixture of the intercalated clay and the functional interpolymer is above 7.
56. The process of claim 55, wherein the base is NaOH or KOH.
57. The process of Claim 1, wherein the step (a) is at a temperature, at an acidic pH, and for a period of time sufficient to produce a chemical bond and/or physical interaction between the cationic moiety of the multifunctional intercalant and the clay; and wherein the step (b) is at a temperature, at a basic pH, and for a period of time sufficient to produce a chemical bond and/or physical interaction between the anionic moiety of the multifunctional intercalant and the functionalized interpolymer.
58. The process of claim 57, wherein the cationic moiety of the multifunctional intercalant forms a linkage with the clay, and wherein the anionic moiety of the multifunctional intercalant forms an ester linkage with the functionalized interpolymer.
59. The process of any one of claim 57 or 58, wherein the multifunctional intercalant is contacted with the clay at a pH of less than 5.
60. The process of any one of claims 57 to 59, wherein the at least partially intercalated clay is contacted with the functionalized interpolymer at a pH
of greater than 8.
61. A process for preparing a nanocomposite composition, comprising the steps of:
contacting a multifunctional intercalant comprising a cationic moiety separated from an anionic moiety by at least 1 carbon atom with a clay at a temperature and for a period of time sufficient to produce an at least partially intercalated clay;
dissolving at least a portion of a functionalized interpolymer in a solvent to produce a functionalized interpolymer mixture; and contacting the at least partially intercalated clay with the functionalized interpolymer mixture at a temperature, and for a period of time sufficient to produce the nanocomposite composition.
62. The process of claim 61, wherein the cationic moiety of the multifunctional intercalant forms a linkage with the clay, and wherein the amonic moiety of the multifunctional intercalant forms an ester linkage with the functionalized interpolymer.
63. A process for preparing a nanocomposite composition, comprising the steps of:
contacting a multifunctional intercalant comprising a cationic moiety separated from an anionic moiety by at least 1 carbon atom with a clay at a temperature, for a period of time, and at an acidic pH sufficient to produce an at least partially intercalated clay;
dissolving at least a portion of a functionalized interpolymer in a solvent to produce a functionalized interpolymer mixture; and contacting the at least partially intercalated clay with the functionalized interpolymer mixture at a temperature, and for a period of time sufficient to produce the nanocomposite composition.
64. The process of claim 63, wherein the cationic moiety of the multifunctional intercalant forms a linkage with the clay, and wherein the anionic moiety of the multifunctional intercalant forms an ester linkage with the functionalized interpolymer.
65. A process for preparing a nanocomposite composition, comprising the steps of:

contacting a multifunctional intercalant comprising a cationic moiety separated from an anionic moiety by at least 1 carbon with a clay in the presence of a cationic surfactant at a temperature, for a period of time, and at an acidic pH sufficient to produce an at least partially intercalated clay;

dissolving at least a portion of a functionalized interpolymer in a solvent to produce a functionalized interpolymer mixture; and contacting the at least partially intercalated clay with the functionalized interpolymer mixture at a temperature, and for a period of time sufficient to produce the nanocomposite composition.
66. The process of claim 65, wherein the cationic moiety of the multifunctional intercalant forms a linkage with the clay, and wherein the anionic moiety of the multifunctional intercalant forms an ester linkage with the functionalized interpolymer.
67. A process for preparing a nanocomposite composition, comprising the steps of:
contacting a multifunctional intercalant comprising a cationic moiety separated from an anionic moiety by at least 1 carbon with a clay in the presence of a cationic surfactant at a temperature, for a period of time, and at an acidic pH sufficient to produce an at least partially intercalated clay;

dissolving at least a portion of a functionalized interpolymer in a solvent to produce a functionalized interpolymer mixture; and contacting the at least partially intercalated clay with the functionalized interpolymer mixture at a pH of greater than 7, at a temperature, and for a period of time sufficient to produce the nanocomposite composition.
68. The process of claim 67, wherein the cationic moiety of the multifunctional intercalant forms a linkage with the clay, and wherein the amonic moiety of the multifunctional intercalant forms an ester linkage with the functionalized interpolymer.
69. The process of any one of claim 67 or 68, further comprising the step of adding a secondary rubber component, a thermoplastic, a filler, a pigment, a curatives, or a combination thereof.
70. The process of any one of claims 67 to 69, further comprising the step of extruding, compression molding, blow molding, drying, solvent removal, grinding, milling, or mixing to produce the nanocomposite composition.
71. An article comprising the nanocomposite composition of any one of claims 1 to 70.
72. The article of 71, wherein the article is injection molded, a fiber, a film, an automotive part, an appliance housing, a consumer product, a packaging article, or a combination thereof.
73. A tire interliner or a tire inner tube comprising the nanocomposite composition of any one of claims 1 to 70.
74. The process of any one of claims 1 to 70, wherein the nanocomposite composition comprises an at least partially intercalated clay having a d100 d-spacing determine using X-ray diffraction of greater than 20 Angstroms.
75. The process of any one of claims 1 to 70, wherein the nanocomposite composition comprises an at least partially intercalated clay having a d100 d-spacing determine using X-ray diffraction of greater than 50 Angstroms.
76. The process of any one of claims 1 to 70, wherein the nanocomposite composition comprises an at least partially intercalated clay having a d100 d-spacing determine using X-ray diffraction of greater than 60 Angstroms.
77. The process of any one of claims 1 to 70, further comprising the step of curing said nanocomposite composition to produce a cured nanocomposite composition.
78. The process of claim 77, wherein said cured nanocomposite composition has a d-spacing determine using X-ray diffraction of greater than 20 Angstroms.
79. The process of any one of claim 77 or 78, wherein said cured nanocomposite composition has an oxygen transmission rate of less than 100 mm-cc/m2 day at 40°C.
80. The process of any one of claims 77 to 79, wherein said cured nanocomposite composition has an oxygen transmission rate of less than 90 mm-cc/m2 day at 40°C.
81. A process for preparing a nanocomposite composition as hereinbefore described with reference to the Examples.
CA2628710A 2005-11-07 2006-09-12 Nanocomposite compositions and processes for making the same Expired - Fee Related CA2628710C (en)

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US11/267,981 US7605205B2 (en) 2005-11-07 2005-11-07 Nanocomposite compositions and processes for making the same
US11/267,981 2005-11-07
PCT/US2006/035266 WO2007055793A2 (en) 2005-11-07 2006-09-12 Nanocomposite compositions and processes for making the same

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JP (1) JP5438972B2 (en)
CN (1) CN101305043B (en)
CA (1) CA2628710C (en)
RU (1) RU2419641C2 (en)
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