AU2009241418B2 - Gel composition, method for preparing the same, and impact resistant absorbing material using the same - Google Patents
Gel composition, method for preparing the same, and impact resistant absorbing material using the same Download PDFInfo
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- AU2009241418B2 AU2009241418B2 AU2009241418A AU2009241418A AU2009241418B2 AU 2009241418 B2 AU2009241418 B2 AU 2009241418B2 AU 2009241418 A AU2009241418 A AU 2009241418A AU 2009241418 A AU2009241418 A AU 2009241418A AU 2009241418 B2 AU2009241418 B2 AU 2009241418B2
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- Australia
- Prior art keywords
- gel composition
- group
- ionic liquid
- composition according
- preparing
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- 239000000203 mixture Substances 0.000 title claims abstract description 128
- 239000011358 absorbing material Substances 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000002608 ionic liquid Substances 0.000 claims abstract description 70
- 239000000178 monomer Substances 0.000 claims abstract description 42
- 229920000642 polymer Polymers 0.000 claims abstract description 34
- 230000002378 acidificating effect Effects 0.000 claims abstract description 16
- 239000007788 liquid Substances 0.000 claims abstract description 13
- 239000000470 constituent Substances 0.000 claims abstract description 10
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 9
- 238000004132 cross linking Methods 0.000 claims abstract description 6
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- -1 phosphoric acid ester anion Chemical class 0.000 claims description 44
- 230000000052 comparative effect Effects 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 150000001450 anions Chemical class 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical group N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 239000003063 flame retardant Substances 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 229920001519 homopolymer Polymers 0.000 claims description 4
- 102100035353 Cyclin-dependent kinase 2-associated protein 1 Human genes 0.000 claims description 2
- 101710176410 Cyclin-dependent kinase 2-associated protein 1 Proteins 0.000 claims description 2
- 101710126767 Filamin A-interacting protein 1-like Proteins 0.000 claims description 2
- 229920002457 flexible plastic Polymers 0.000 claims 1
- 239000002985 plastic film Substances 0.000 claims 1
- 239000000499 gel Substances 0.000 description 94
- 229920001451 polypropylene glycol Polymers 0.000 description 20
- 239000000126 substance Substances 0.000 description 18
- 239000011347 resin Substances 0.000 description 15
- 229920005989 resin Polymers 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 230000001133 acceleration Effects 0.000 description 8
- 150000001768 cations Chemical class 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000035939 shock Effects 0.000 description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000010276 construction Methods 0.000 description 4
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229920002379 silicone rubber Polymers 0.000 description 4
- 239000004945 silicone rubber Substances 0.000 description 4
- 229920002799 BoPET Polymers 0.000 description 3
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940048053 acrylate Drugs 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- UYVHLQMAHUNPNC-UHFFFAOYSA-N ethylsulfonyl prop-2-eneperoxoate Chemical compound CCS(=O)(=O)OOC(=O)C=C UYVHLQMAHUNPNC-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 125000005936 piperidyl group Chemical group 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 150000003512 tertiary amines Chemical group 0.000 description 3
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 229920002063 Sorbothane Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920006311 Urethane elastomer Polymers 0.000 description 2
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- SXBYWGRUMVGTAI-UHFFFAOYSA-N dimethyl(3-prop-2-enoyloxypropyl)azanium;bromide Chemical compound [Br-].C[NH+](C)CCCOC(=O)C=C SXBYWGRUMVGTAI-UHFFFAOYSA-N 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- ZJXZSIYSNXKHEA-UHFFFAOYSA-L ethyl phosphate(2-) Chemical compound CCOP([O-])([O-])=O ZJXZSIYSNXKHEA-UHFFFAOYSA-L 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- WPTSMKAKCDGTOV-UHFFFAOYSA-N ethylsulfonyl 2-methylprop-2-eneperoxoate Chemical compound CCS(=O)(=O)OOC(=O)C(C)=C WPTSMKAKCDGTOV-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000011245 gel electrolyte Substances 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- UPPUJFRSINZXTE-UHFFFAOYSA-N (2,2,3,3,4-pentamethylpiperidin-1-yl) 2-methylprop-2-enoate Chemical compound CC1CCN(OC(=O)C(C)=C)C(C)(C)C1(C)C UPPUJFRSINZXTE-UHFFFAOYSA-N 0.000 description 1
- HKTVJXTZAPGBRT-UHFFFAOYSA-N (2,2,3,3,4-pentamethylpiperidin-1-yl) prop-2-enoate Chemical compound CC1CCN(OC(=O)C=C)C(C)(C)C1(C)C HKTVJXTZAPGBRT-UHFFFAOYSA-N 0.000 description 1
- RPNDKNJEUSJAMT-UHFFFAOYSA-N (2,2,3,3-tetramethylpiperidin-1-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)ON1CCCC(C)(C)C1(C)C RPNDKNJEUSJAMT-UHFFFAOYSA-N 0.000 description 1
- LJBVVBVQVFLVSK-UHFFFAOYSA-N (2-hydroxy-3-prop-2-enoyloxypropyl)-dimethylazanium;fluoride Chemical compound [F-].C[NH+](C)CC(O)COC(=O)C=C LJBVVBVQVFLVSK-UHFFFAOYSA-N 0.000 description 1
- MQKJKEURBRSXOE-UHFFFAOYSA-N (2-hydroxy-3-prop-2-enoyloxypropyl)-dimethylazanium;iodide Chemical compound [I-].C[NH+](C)CC(O)COC(=O)C=C MQKJKEURBRSXOE-UHFFFAOYSA-N 0.000 description 1
- LDDPKTUBASWMTR-UHFFFAOYSA-M (2-hydroxy-3-prop-2-enoyloxypropyl)-trimethylazanium;bromide Chemical compound [Br-].C[N+](C)(C)CC(O)COC(=O)C=C LDDPKTUBASWMTR-UHFFFAOYSA-M 0.000 description 1
- KQSXCARHPXBHGH-UHFFFAOYSA-M (2-hydroxy-3-prop-2-enoyloxypropyl)-trimethylazanium;fluoride Chemical compound [F-].C[N+](C)(C)CC(O)COC(=O)C=C KQSXCARHPXBHGH-UHFFFAOYSA-M 0.000 description 1
- LNMAAVUPXBUMQM-UHFFFAOYSA-M (2-hydroxy-3-prop-2-enoyloxypropyl)-trimethylazanium;iodide Chemical compound [I-].C[N+](C)(C)CC(O)COC(=O)C=C LNMAAVUPXBUMQM-UHFFFAOYSA-M 0.000 description 1
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- HDANPERKVWZPFC-UHFFFAOYSA-N 1-prop-2-enoyloxypropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(=O)C=C HDANPERKVWZPFC-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-O 1H-indol-1-ium Chemical compound C1=CC=C2[NH2+]C=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-O 0.000 description 1
- MCSUEOOWIISFQB-UHFFFAOYSA-N 1h-imidazol-3-ium;2-phenylethenesulfonate Chemical compound C1=C[NH+]=CN1.[O-]S(=O)(=O)C=CC1=CC=CC=C1 MCSUEOOWIISFQB-UHFFFAOYSA-N 0.000 description 1
- NEBBLNDVSSWJLL-UHFFFAOYSA-N 2,3-bis(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCC(OC(=O)C(C)=C)COC(=O)C(C)=C NEBBLNDVSSWJLL-UHFFFAOYSA-N 0.000 description 1
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 1
- FCZRAAJZTGOYIC-UHFFFAOYSA-N 2,4-dimethylpent-2-enamide Chemical compound CC(C)C=C(C)C(N)=O FCZRAAJZTGOYIC-UHFFFAOYSA-N 0.000 description 1
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
- JJBFVQSGPLGDNX-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(=O)C(C)=C JJBFVQSGPLGDNX-UHFFFAOYSA-N 0.000 description 1
- UECGJSXCVLTIMQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxycarbonyl)cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1C(=O)OCCOC(=O)C=C UECGJSXCVLTIMQ-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- HYTWSJWXLMPIKR-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate;hydrobromide Chemical compound [Br-].C[NH+](C)CCOC(=O)C(C)=C HYTWSJWXLMPIKR-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- UXYOXQQBQOISHC-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate;3-(dimethylamino)propyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C.CN(C)CCCOC(=O)C=C UXYOXQQBQOISHC-UHFFFAOYSA-N 0.000 description 1
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- IFFXVVFRFDGXEC-UHFFFAOYSA-M trimethyl(4-prop-2-enoyloxybutyl)azanium;fluoride Chemical compound [F-].C[N+](C)(C)CCCCOC(=O)C=C IFFXVVFRFDGXEC-UHFFFAOYSA-M 0.000 description 1
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- USFMMZYROHDWPJ-UHFFFAOYSA-N trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium Chemical compound CC(=C)C(=O)OCC[N+](C)(C)C USFMMZYROHDWPJ-UHFFFAOYSA-N 0.000 description 1
- FGKCGMMQJOWMFW-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;bromide Chemical compound [Br-].CC(=C)C(=O)OCC[N+](C)(C)C FGKCGMMQJOWMFW-UHFFFAOYSA-M 0.000 description 1
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- IZYCXLQBOZUYAR-UHFFFAOYSA-M trimethyl-[3-(2-methylprop-2-enoyloxy)propyl]azanium;bromide Chemical compound [Br-].CC(=C)C(=O)OCCC[N+](C)(C)C IZYCXLQBOZUYAR-UHFFFAOYSA-M 0.000 description 1
- NFUDTVOYLQNLPF-UHFFFAOYSA-M trimethyl-[3-(2-methylprop-2-enoyloxy)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCCC[N+](C)(C)C NFUDTVOYLQNLPF-UHFFFAOYSA-M 0.000 description 1
- NWPVKLLZJAHTCR-UHFFFAOYSA-M trimethyl-[3-(2-methylprop-2-enoyloxy)propyl]azanium;fluoride Chemical compound [F-].CC(=C)C(=O)OCCC[N+](C)(C)C NWPVKLLZJAHTCR-UHFFFAOYSA-M 0.000 description 1
- GTLXKMNTNRDVBP-UHFFFAOYSA-M trimethyl-[3-(2-methylprop-2-enoyloxy)propyl]azanium;iodide Chemical compound [I-].CC(=C)C(=O)OCCC[N+](C)(C)C GTLXKMNTNRDVBP-UHFFFAOYSA-M 0.000 description 1
- CCOFJZCCFGTMOZ-UHFFFAOYSA-N trimethyl-[4-(2-methylprop-2-enoyloxy)butyl]azanium Chemical compound CC(=C)C(=O)OCCCC[N+](C)(C)C CCOFJZCCFGTMOZ-UHFFFAOYSA-N 0.000 description 1
- JIQWUPNEOSUGBI-UHFFFAOYSA-M trimethyl-[4-(2-methylprop-2-enoyloxy)butyl]azanium;bromide Chemical compound [Br-].CC(=C)C(=O)OCCCC[N+](C)(C)C JIQWUPNEOSUGBI-UHFFFAOYSA-M 0.000 description 1
- PXVADEPLHHVAKQ-UHFFFAOYSA-M trimethyl-[4-(2-methylprop-2-enoyloxy)butyl]azanium;fluoride Chemical compound [F-].CC(=C)C(=O)OCCCC[N+](C)(C)C PXVADEPLHHVAKQ-UHFFFAOYSA-M 0.000 description 1
- VZYLIBJEHQPXSN-UHFFFAOYSA-M trimethyl-[4-(2-methylprop-2-enoyloxy)butyl]azanium;iodide Chemical compound [I-].CC(=C)C(=O)OCCCC[N+](C)(C)C VZYLIBJEHQPXSN-UHFFFAOYSA-M 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/5205—Salts of P-acids with N-bases
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Fluid-Damping Devices (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008120384A JP2009269974A (ja) | 2008-05-02 | 2008-05-02 | ゲル状組成物とその製造方法、およびそれを用いた衝撃吸収材 |
| JP2008-120384 | 2008-05-02 | ||
| PCT/US2009/041693 WO2009134694A2 (en) | 2008-05-02 | 2009-04-24 | Gel composition, method for preparing the same, and impact resistant absorbing material using the same |
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| AU2009241418A1 AU2009241418A1 (en) | 2009-11-05 |
| AU2009241418B2 true AU2009241418B2 (en) | 2012-08-23 |
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| EP (1) | EP2285900A4 (enExample) |
| JP (1) | JP2009269974A (enExample) |
| CN (1) | CN102066486B (enExample) |
| AU (1) | AU2009241418B2 (enExample) |
| WO (1) | WO2009134694A2 (enExample) |
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| KR101783062B1 (ko) | 2009-08-28 | 2017-09-28 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 다작용성 양이온을 포함하는 중합성 이온성 액체 및 정전기 방지 코팅 |
| KR20120068009A (ko) | 2009-08-28 | 2012-06-26 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 중합성 이온성 액체 혼합물을 포함하는 조성물 및 물품, 및 경화 방법 |
| RU2012131166A (ru) | 2009-12-22 | 2014-01-27 | 3М Инновейтив Пропертиз Компани | Отверждаемые стоматологические композиции и изделия, содержащие полимеризуемые ионные жидкости |
| JP5818879B2 (ja) | 2010-05-18 | 2015-11-18 | スリーエム イノベイティブ プロパティズ カンパニー | 芳香族カルボキシレートアニオンを含む重合性イオン液体 |
| WO2011146326A1 (en) * | 2010-05-18 | 2011-11-24 | 3M Innovative Properties Company | Polymerizable ionic liquid compositions |
| JP5818079B2 (ja) * | 2011-08-31 | 2015-11-18 | Dic株式会社 | 高分子複合体 |
| US20130137790A1 (en) * | 2011-11-30 | 2013-05-30 | Nike, Inc. | Impact-Resistant Foam Composition |
| JP2015117252A (ja) * | 2012-03-30 | 2015-06-25 | 国立大学法人 東京大学 | イオン液体含有ゲルの製造方法 |
| US8629048B1 (en) | 2012-07-06 | 2014-01-14 | Micron Technology, Inc. | Methods of forming a pattern on a substrate |
| JP6836900B6 (ja) * | 2013-05-02 | 2021-03-31 | スリーエム イノベイティブ プロパティズ カンパニー | 部分フッ素化エラストマー並びにその製造方法及びその使用方法 |
| WO2014182128A1 (ko) * | 2013-05-09 | 2014-11-13 | 주식회사 엘지화학 | 고흡수성 수지의 제조방법 |
| KR101604272B1 (ko) | 2013-05-09 | 2016-03-25 | 주식회사 엘지화학 | 고흡수성 수지의 제조방법 |
| JP6454192B2 (ja) * | 2015-03-20 | 2019-01-16 | 株式会社沖データ | 画像形成ユニットおよび画像形成装置 |
| US10004929B2 (en) | 2015-10-16 | 2018-06-26 | Ge-Hitachi Nuclear Energy Americas Llc | Passive fire response system and method of manufacturing |
| CN106632775A (zh) * | 2016-09-13 | 2017-05-10 | 西安交通大学 | 一种力学性能优良、高透光且自愈合的离子液体凝胶的制备方法 |
| IT201700051624A1 (it) * | 2017-05-12 | 2018-11-12 | U Invest S R L | Scarpa di sicurezza defaticante. |
| US12250984B2 (en) | 2018-01-31 | 2025-03-18 | Asics Corporation | Shoe sole member and shoe |
| EP3747296A4 (en) * | 2018-01-31 | 2021-03-31 | ASICS Corporation | FOOTWEAR AND SHOE ELEMENT |
| EP3845600B1 (en) * | 2018-08-30 | 2022-10-26 | Denka Company Limited | Electroconductive resin composition and molded article of same |
| CN112080133B (zh) * | 2020-09-21 | 2022-05-17 | 苏州大学 | 可3d打印且透明的导电离子凝胶及其制备和应用 |
| CN113540558B (zh) * | 2021-07-16 | 2023-12-26 | 北京工商大学 | 一种具备热关闭功能的阻燃聚合物电解质及其制备方法 |
| CN115536875A (zh) * | 2022-09-20 | 2022-12-30 | 北京化工大学 | 一种静电-化学双交联型聚硅氧烷羧酸铵盐离子凝胶 |
| WO2025115995A1 (ja) * | 2023-11-30 | 2025-06-05 | 大阪有機化学工業株式会社 | 硬化性樹脂組成物、当該組成物を硬化させた絶縁性硬化膜、及び、当該絶縁性硬化膜を備えたディスプレイデバイス |
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- 2009-04-24 EP EP09739496.9A patent/EP2285900A4/en not_active Withdrawn
- 2009-04-24 WO PCT/US2009/041693 patent/WO2009134694A2/en not_active Ceased
- 2009-04-24 AU AU2009241418A patent/AU2009241418B2/en not_active Ceased
- 2009-04-24 CN CN2009801235637A patent/CN102066486B/zh not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2285900A4 (en) | 2017-06-14 |
| US8461237B2 (en) | 2013-06-11 |
| CN102066486A (zh) | 2011-05-18 |
| US20110097585A1 (en) | 2011-04-28 |
| AU2009241418A1 (en) | 2009-11-05 |
| JP2009269974A (ja) | 2009-11-19 |
| CN102066486B (zh) | 2013-08-14 |
| EP2285900A2 (en) | 2011-02-23 |
| WO2009134694A3 (en) | 2009-12-23 |
| WO2009134694A2 (en) | 2009-11-05 |
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