CA2631692C - Elastomer nanocomposites comprising isobutylene and multifunctional oligomers - Google Patents
Elastomer nanocomposites comprising isobutylene and multifunctional oligomers Download PDFInfo
- Publication number
- CA2631692C CA2631692C CA2631692A CA2631692A CA2631692C CA 2631692 C CA2631692 C CA 2631692C CA 2631692 A CA2631692 A CA 2631692A CA 2631692 A CA2631692 A CA 2631692A CA 2631692 C CA2631692 C CA 2631692C
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- Canada
- Prior art keywords
- acid
- nanocomposite
- polymer
- elastomer
- clay
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920001971 elastomer Polymers 0.000 title claims abstract description 184
- 239000002114 nanocomposite Substances 0.000 title claims abstract description 149
- 239000000806 elastomer Substances 0.000 title claims abstract description 113
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims description 33
- 229920000642 polymer Polymers 0.000 claims abstract description 129
- 239000000203 mixture Substances 0.000 claims abstract description 112
- 239000004927 clay Substances 0.000 claims abstract description 108
- 239000002253 acid Substances 0.000 claims abstract description 66
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 30
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 5
- -1 ammonium ions Chemical class 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 52
- 229920006112 polar polymer Polymers 0.000 claims description 26
- 150000001412 amines Chemical class 0.000 claims description 22
- 150000008064 anhydrides Chemical class 0.000 claims description 19
- 239000006229 carbon black Substances 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 150000002170 ethers Chemical class 0.000 claims description 13
- 150000002825 nitriles Chemical class 0.000 claims description 13
- 235000021355 Stearic acid Nutrition 0.000 claims description 12
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 12
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 12
- 239000008117 stearic acid Substances 0.000 claims description 12
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 11
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 10
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 8
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 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 claims description 7
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 6
- 229910021647 smectite Inorganic materials 0.000 claims description 6
- 229940014800 succinic anhydride Drugs 0.000 claims description 6
- 229910052902 vermiculite Inorganic materials 0.000 claims description 6
- 239000010455 vermiculite Substances 0.000 claims description 6
- 235000019354 vermiculite Nutrition 0.000 claims description 6
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 5
- 150000004760 silicates Chemical class 0.000 claims description 5
- 239000011787 zinc oxide Substances 0.000 claims description 5
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- WIGBIRJTZOHFID-UHFFFAOYSA-N azinic acid Chemical compound O[NH2+][O-] WIGBIRJTZOHFID-UHFFFAOYSA-N 0.000 claims description 4
- LUCMUCKPKZWJHC-UHFFFAOYSA-N azonic acid Chemical compound O[NH+](O)[O-] LUCMUCKPKZWJHC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000440 bentonite Substances 0.000 claims description 4
- 229910000278 bentonite Inorganic materials 0.000 claims description 4
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
- VNSBYDPZHCQWNB-UHFFFAOYSA-N calcium;aluminum;dioxido(oxo)silane;sodium;hydrate Chemical compound O.[Na].[Al].[Ca+2].[O-][Si]([O-])=O VNSBYDPZHCQWNB-UHFFFAOYSA-N 0.000 claims description 4
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 229910052621 halloysite Inorganic materials 0.000 claims description 4
- 239000012760 heat stabilizer Substances 0.000 claims description 4
- 229910000271 hectorite Inorganic materials 0.000 claims description 4
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 claims description 4
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 4
- 229960001545 hydrotalcite Drugs 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 229940094522 laponite Drugs 0.000 claims description 4
- 239000004611 light stabiliser Substances 0.000 claims description 4
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 claims description 4
- 239000010445 mica Substances 0.000 claims description 4
- 229910052618 mica group Inorganic materials 0.000 claims description 4
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 4
- 229910000273 nontronite Inorganic materials 0.000 claims description 4
- 150000001451 organic peroxides Chemical class 0.000 claims description 4
- 150000004965 peroxy acids Chemical class 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- 229910000275 saponite Inorganic materials 0.000 claims description 4
- 229910000276 sauconite Inorganic materials 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 claims description 4
- 239000000454 talc Substances 0.000 claims description 4
- 229910052623 talc Inorganic materials 0.000 claims description 4
- 150000003566 thiocarboxylic acids Chemical class 0.000 claims description 4
- 239000004408 titanium dioxide Substances 0.000 claims description 4
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 3
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 claims 1
- 230000004888 barrier function Effects 0.000 abstract description 16
- 239000005060 rubber Substances 0.000 description 71
- 239000000243 solution Substances 0.000 description 44
- 239000002904 solvent Substances 0.000 description 30
- 229920001577 copolymer Polymers 0.000 description 26
- 229920005555 halobutyl Polymers 0.000 description 24
- 239000000178 monomer Substances 0.000 description 24
- 230000008569 process Effects 0.000 description 24
- 229920005549 butyl rubber Polymers 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 238000002156 mixing Methods 0.000 description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 19
- 239000000945 filler Substances 0.000 description 19
- 229910052760 oxygen Inorganic materials 0.000 description 19
- 239000001301 oxygen Substances 0.000 description 19
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 18
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 18
- 239000000654 additive Substances 0.000 description 17
- 229910052794 bromium Inorganic materials 0.000 description 17
- 125000000524 functional group Chemical group 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 239000000839 emulsion Substances 0.000 description 15
- 230000035699 permeability Effects 0.000 description 14
- 150000001336 alkenes Chemical class 0.000 description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 230000005540 biological transmission Effects 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000005062 Polybutadiene Substances 0.000 description 9
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 9
- 238000004299 exfoliation Methods 0.000 description 9
- 230000026030 halogenation Effects 0.000 description 9
- 238000005658 halogenation reaction Methods 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229920002367 Polyisobutene Polymers 0.000 description 8
- 229920005557 bromobutyl Polymers 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000011877 solvent mixture Substances 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 238000009830 intercalation Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 229920002857 polybutadiene Polymers 0.000 description 7
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 6
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 244000043261 Hevea brasiliensis Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 238000007906 compression Methods 0.000 description 6
- 230000006835 compression Effects 0.000 description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- 238000007306 functionalization reaction Methods 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- 230000002687 intercalation Effects 0.000 description 6
- 229920003052 natural elastomer Polymers 0.000 description 6
- 229920001194 natural rubber Polymers 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 229920002943 EPDM rubber Polymers 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 229920005556 chlorobutyl Polymers 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 229910001415 sodium ion Inorganic materials 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
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- MHNNAWXXUZQSNM-UHFFFAOYSA-N methylethylethylene Natural products CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 4
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- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 3
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- 229960002447 thiram Drugs 0.000 description 3
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- TUFJPPAQOXUHRI-KTKRTIGZSA-N n'-[(z)-octadec-9-enyl]propane-1,3-diamine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCCCN TUFJPPAQOXUHRI-KTKRTIGZSA-N 0.000 description 1
- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 1
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- HOBBGWUQJYXTQU-UHFFFAOYSA-N sulfurodithioic O,O-acid Chemical class OS(O)(=S)=S HOBBGWUQJYXTQU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
- C08L23/28—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with halogens or halogen-containing compounds
- C08L23/286—Chlorinated polyethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/06—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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| US11/293,561 | 2005-12-02 | ||
| US11/293,561 US7632886B2 (en) | 2005-12-02 | 2005-12-02 | Elastomer nanocomposites comprising isobutylene and multifunctional oligomers |
| PCT/US2006/038785 WO2007064400A1 (en) | 2005-12-02 | 2006-10-04 | Elastomer nanocomposites comprising isobutylene and multifunctional oligomers |
Publications (2)
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| CA2631692A1 CA2631692A1 (en) | 2007-06-07 |
| CA2631692C true CA2631692C (en) | 2011-09-06 |
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|---|---|---|---|
| CA2631692A Expired - Fee Related CA2631692C (en) | 2005-12-02 | 2006-10-04 | Elastomer nanocomposites comprising isobutylene and multifunctional oligomers |
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|---|---|
| US (1) | US7632886B2 (enExample) |
| EP (1) | EP1954755B8 (enExample) |
| JP (1) | JP5419257B2 (enExample) |
| CN (1) | CN101316888B (enExample) |
| CA (1) | CA2631692C (enExample) |
| RU (1) | RU2430122C2 (enExample) |
| WO (1) | WO2007064400A1 (enExample) |
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| JP4683928B2 (ja) * | 2002-12-18 | 2011-05-18 | 株式会社ブリヂストン | クレイの剥離方法、該方法から得られた組成物、及び該組成物を含む変性ゴム |
| US7572855B2 (en) * | 2005-01-28 | 2009-08-11 | Bridgestone Corporation | Nano-composite and compositions manufactured thereof |
| US7579398B2 (en) | 2005-02-02 | 2009-08-25 | Bridgestone Corporation | Nano-composite and compositions therefrom |
| CN101472987A (zh) * | 2006-02-15 | 2009-07-01 | 戴维·J·柴科 | 聚合物复合材料，聚合物纳米复合材料和方法 |
| US7935184B2 (en) | 2006-06-19 | 2011-05-03 | Bridgestone Corporation | Method of preparing imidazolium surfactants |
| US9573347B2 (en) * | 2009-12-15 | 2017-02-21 | Teknor Apex Company | Thermoplastic elastomer with desirable grip especially during wet conditions |
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| UA69800U (ru) * | 2011-11-16 | 2012-05-10 | Федор Петрович Бережный | Способ получения "нанополипропилена" - нанокомпозитов полипропилена и сополимеров полипропилена |
| JP6018951B2 (ja) * | 2013-02-28 | 2016-11-02 | 株式会社ブリヂストン | ゴム組成物、インナーライナー素材、及び、空気入りタイヤ |
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| WO2019213226A1 (en) | 2018-05-04 | 2019-11-07 | Bridgestone Americas Tire Operations, Llc | Tire tread rubber composition |
| WO2019213233A1 (en) | 2018-05-04 | 2019-11-07 | Bridgestone Americas Tire Operations, Llc | Tire tread rubber composition |
| EP3788103A4 (en) | 2018-05-04 | 2022-01-12 | Bridgestone Americas Tire Operations, LLC | RUBBER COMPOSITION FOR TIRE TREAD |
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| US6417262B1 (en) | 1998-12-07 | 2002-07-09 | Eastman Chemical Company | High barrier amorphous polyamide-clay nanocomposite and a process for preparing same |
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| ATE296332T1 (de) * | 1999-12-29 | 2005-06-15 | Dow Global Technologies Inc | Thermoplastisches nanokomposit auf basis von polypropylen und dessen herstellung |
| WO2001085831A2 (en) | 2000-05-05 | 2001-11-15 | The Dow Chemical Company | Functionalized polymer nanocomposites |
| US6770697B2 (en) | 2001-02-20 | 2004-08-03 | Solvay Engineered Polymers | High melt-strength polyolefin composites and methods for making and using same |
| JP2002264263A (ja) * | 2001-03-08 | 2002-09-18 | Asahi Kasei Corp | 積層体 |
| ATE423806T1 (de) | 2001-06-08 | 2009-03-15 | Exxonmobil Chem Patents Inc | Nanoverbundwerkstoffe mit geringer permeabilität |
| WO2002100936A1 (en) | 2001-06-13 | 2002-12-19 | Exxonmobil Chemical Patents Inc. | Low permeability nanocomposites |
| JP4162519B2 (ja) * | 2002-03-27 | 2008-10-08 | 横浜ゴム株式会社 | 有機化処理された層状粘土鉱物並びにそれを含む有機重合体組成物及びタイヤ用インナーライナー |
| JP4043283B2 (ja) * | 2002-05-21 | 2008-02-06 | 横浜ゴム株式会社 | 空気入りタイヤ用ゴム組成物 |
| EP1527127B1 (en) * | 2002-07-05 | 2009-02-11 | Exxonmobil Chemical Patents Inc. | Functionalized elastomer nanocomposite |
| JP4683928B2 (ja) * | 2002-12-18 | 2011-05-18 | 株式会社ブリヂストン | クレイの剥離方法、該方法から得られた組成物、及び該組成物を含む変性ゴム |
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| CA2631692A1 (en) | 2007-06-07 |
| US7632886B2 (en) | 2009-12-15 |
| CN101316888A (zh) | 2008-12-03 |
| WO2007064400A1 (en) | 2007-06-07 |
| JP5419257B2 (ja) | 2014-02-19 |
| US20070129477A1 (en) | 2007-06-07 |
| RU2008126740A (ru) | 2010-01-10 |
| JP2009517524A (ja) | 2009-04-30 |
| RU2430122C2 (ru) | 2011-09-27 |
| CN101316888B (zh) | 2013-10-23 |
| EP1954755B8 (en) | 2017-10-18 |
| EP1954755A1 (en) | 2008-08-13 |
| EP1954755B1 (en) | 2017-09-13 |
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