CA2223350A1

CA2223350A1 - Intercalates and exfoliates formed with long chain (c6+) or aromatic matrix polymer-compatible monomeric, oligomeric or polymeric intercalant compounds; and composite materials containing same

Intercalates and exfoliates formed with long chain (c6+) or aromatic matrix polymer-compatible monomeric, oligomeric or polymeric intercalant compounds; and composite materials containing same Download PDF

Info

Publication number: CA2223350A1
Authority: CA; Canada
Prior art keywords: intercalant; weight; phyllosilicate; surface modifier; composition
Prior art date: 1996-12-06
Legal status : Abandoned

Application number

CA002223350A

Other languages

English (en)

French (fr)

Inventor

Semeon Tsipursky

Gary W. Beall

Ying Liang

Tie Lan

Current Assignee

Amcol International Corp

Original Assignee

Amcol International Corp

Priority date

1996-12-06

Filing date

1997-12-03

Publication date

1998-06-06

1996-12-06 Priority claimed from US08/758,740 external-priority patent/US5952095A/en

1997-12-03 Application filed by Amcol International Corp filed Critical Amcol International Corp

1998-06-06 Publication of CA2223350A1 publication Critical patent/CA2223350A1/en

Status Abandoned legal-status Critical Current

Links

239000011159 matrix material Substances 0.000 title claims abstract description 96
150000001875 compounds Chemical class 0.000 title claims abstract description 84
125000003118 aryl group Chemical group 0.000 title claims abstract description 57
239000002131 composite material Substances 0.000 title claims description 18
239000000203 mixture Substances 0.000 claims abstract description 197
239000000463 material Substances 0.000 claims abstract description 133
229910052615 phyllosilicate Inorganic materials 0.000 claims abstract description 109
229920000642 polymer Polymers 0.000 claims abstract description 104
239000003607 modifier Substances 0.000 claims abstract description 64
239000007788 liquid Substances 0.000 claims abstract description 22
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
125000000524 functional group Chemical group 0.000 claims abstract description 14
-1 polyethylene terephthalate Polymers 0.000 claims description 201
238000009830 intercalation Methods 0.000 claims description 106
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 62
239000011229 interlayer Substances 0.000 claims description 47
238000000034 method Methods 0.000 claims description 38
150000001768 cations Chemical class 0.000 claims description 35
239000010410 layer Substances 0.000 claims description 35
238000001179 sorption measurement Methods 0.000 claims description 31
230000002687 intercalation Effects 0.000 claims description 26
230000000536 complexating effect Effects 0.000 claims description 25
239000000178 monomer Substances 0.000 claims description 22
229920001169 thermoplastic Polymers 0.000 claims description 13
239000004952 Polyamide Substances 0.000 claims description 11
239000003960 organic solvent Substances 0.000 claims description 11
229920002647 polyamide Polymers 0.000 claims description 11
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 10
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 10
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 10
229920001187 thermosetting polymer Polymers 0.000 claims description 10
239000006087 Silane Coupling Agent Substances 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 8
229920002451 polyvinyl alcohol Polymers 0.000 claims description 8
239000004416 thermosoftening plastic Substances 0.000 claims description 8
150000004010 onium ions Chemical class 0.000 claims description 7
239000004634 thermosetting polymer Substances 0.000 claims description 7
239000004372 Polyvinyl alcohol Substances 0.000 claims description 6
229920000139 polyethylene terephthalate Polymers 0.000 claims description 6
239000005020 polyethylene terephthalate Substances 0.000 claims description 6
230000032798 delamination Effects 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
238000005411 Van der Waals force Methods 0.000 claims description 4
230000009920 chelation Effects 0.000 claims description 4
239000007822 coupling agent Substances 0.000 claims description 4
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239000004593 Epoxy Substances 0.000 claims description 3
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239000004417 polycarbonate Substances 0.000 claims description 3
XRBXGZZMKCBTFP-UHFFFAOYSA-N 4-(2,2-dihydroxyethoxycarbonyl)benzoic acid Chemical compound OC(O)COC(=O)C1=CC=C(C(O)=O)C=C1 XRBXGZZMKCBTFP-UHFFFAOYSA-N 0.000 claims 2
CBLGXJKSPMNSRJ-UHFFFAOYSA-N 4-(4,4-dihydroxybutoxycarbonyl)benzoic acid Chemical compound OC(O)CCCOC(=O)C1=CC=C(C(O)=O)C=C1 CBLGXJKSPMNSRJ-UHFFFAOYSA-N 0.000 claims 2
VKFCWJMAWJAOAH-UHFFFAOYSA-N 4-(3-hydroxypropoxycarbonyl)benzoic acid Chemical compound OCCCOC(=O)C1=CC=C(C(O)=O)C=C1 VKFCWJMAWJAOAH-UHFFFAOYSA-N 0.000 claims 1
JJVHCGKLZWAWKQ-UHFFFAOYSA-N 4-(5-hydroxypentoxycarbonyl)benzoic acid Chemical compound OCCCCCOC(=O)C1=CC=C(C(O)=O)C=C1 JJVHCGKLZWAWKQ-UHFFFAOYSA-N 0.000 claims 1
JFFQXJXLNZADOF-UHFFFAOYSA-N 4-ethoxycarbonylbenzenecarboperoxoic acid Chemical compound CCOC(=O)C1=CC=C(C(=O)OO)C=C1 JFFQXJXLNZADOF-UHFFFAOYSA-N 0.000 claims 1
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239000012876 carrier material Substances 0.000 abstract description 4
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238000004299 exfoliation Methods 0.000 description 27
239000002904 solvent Substances 0.000 description 27
150000007513 acids Chemical class 0.000 description 22
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 22
229910052901 montmorillonite Inorganic materials 0.000 description 20
150000002148 esters Chemical class 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
239000002114 nanocomposite Substances 0.000 description 17
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150000001408 amides Chemical class 0.000 description 16
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BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 15
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230000001965 increasing effect Effects 0.000 description 13
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239000002184 metal Substances 0.000 description 13
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150000001299 aldehydes Chemical class 0.000 description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
150000002894 organic compounds Chemical class 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 11
150000001298 alcohols Chemical class 0.000 description 10
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150000003951 lactams Chemical class 0.000 description 10
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239000004677 Nylon Substances 0.000 description 9
238000002441 X-ray diffraction Methods 0.000 description 9
125000004429 atom Chemical group 0.000 description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
150000002576 ketones Chemical class 0.000 description 9
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 9
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239000000243 solution Substances 0.000 description 9
FUJGBKOREIZSDD-KTKRTIGZSA-N 1-[(z)-octadec-9-enyl]pyrrolidin-2-one Chemical compound CCCCCCCC\C=C/CCCCCCCCN1CCCC1=O FUJGBKOREIZSDD-KTKRTIGZSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
150000008064 anhydrides Chemical class 0.000 description 8
239000003814 drug Substances 0.000 description 8
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238000011068 loading method Methods 0.000 description 8
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230000008569 process Effects 0.000 description 8
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
NJPQAIBZIHNJDO-UHFFFAOYSA-N 1-dodecylpyrrolidin-2-one Chemical compound CCCCCCCCCCCCN1CCCC1=O NJPQAIBZIHNJDO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000011575 calcium Substances 0.000 description 6
229910052791 calcium Inorganic materials 0.000 description 6
239000002537 cosmetic Substances 0.000 description 6
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238000006116 polymerization reaction Methods 0.000 description 6
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OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
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ARKHFOXARSJRGJ-UHFFFAOYSA-N 1-(6-aminohexyl)pyrrolidin-2-one Chemical compound NCCCCCCN1CCCC1=O ARKHFOXARSJRGJ-UHFFFAOYSA-N 0.000 description 4
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QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
239000000314 lubricant Substances 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
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238000001819 mass spectrum Methods 0.000 description 4
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MMINFSMURORWKH-UHFFFAOYSA-N 3,6-dioxabicyclo[6.2.2]dodeca-1(10),8,11-triene-2,7-dione Chemical compound O=C1OCCOC(=O)C2=CC=C1C=C2 MMINFSMURORWKH-UHFFFAOYSA-N 0.000 description 3
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
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HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 2
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