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)
- Fluid-Damping Devices (AREA)
- Processes Of Treating Macromolecular Substances (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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| US (1) | US8461237B2 (https=) |
| EP (1) | EP2285900A4 (https=) |
| JP (1) | JP2009269974A (https=) |
| CN (1) | CN102066486B (https=) |
| AU (1) | AU2009241418B2 (https=) |
| WO (1) | WO2009134694A2 (https=) |
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| EP2470509A2 (en) | 2009-08-28 | 2012-07-04 | 3M Innovative Properties Company | Compositions and articles comprising polymerizable ionic liquid mixture, and methods of curing |
| CN103168026B (zh) | 2009-08-28 | 2016-06-29 | 3M创新有限公司 | 包含多官能阳离子的可聚合离子液体及抗静电涂料 |
| EP2515827A2 (en) | 2009-12-22 | 2012-10-31 | 3M Innovative Properties Company | Curable dental compositions and articles comprising polymerizable ionic liquids |
| WO2011146326A1 (en) * | 2010-05-18 | 2011-11-24 | 3M Innovative Properties Company | Polymerizable ionic liquid compositions |
| 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 |
| JP5818079B2 (ja) * | 2011-08-31 | 2015-11-18 | Dic株式会社 | 高分子複合体 |
| WO2013082444A1 (en) * | 2011-11-30 | 2013-06-06 | Nike International Ltd. | 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 |
| KR101604272B1 (ko) | 2013-05-09 | 2016-03-25 | 주식회사 엘지화학 | 고흡수성 수지의 제조방법 |
| EP2829566B2 (en) * | 2013-05-09 | 2020-05-27 | LG Chem, Ltd. | Preparation method for super absorbent resin |
| 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. |
| JP6830166B2 (ja) | 2018-01-31 | 2021-02-17 | 株式会社アシックス | 靴底用部材及び靴 |
| JP6899930B2 (ja) * | 2018-01-31 | 2021-07-07 | 株式会社アシックス | 靴底用部材及び靴 |
| CN112601786B (zh) * | 2018-08-30 | 2023-05-05 | 电化株式会社 | 导电性树脂组合物及其成型品 |
| 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 |
| TW202544055A (zh) * | 2023-11-30 | 2025-11-16 | 日商大阪有機化學工業股份有限公司 | 固化性樹脂組合物、使該組合物固化而成的絕緣性固化膜以及具備該絕緣性固化膜的顯示裝置 |
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- 2009-04-24 WO PCT/US2009/041693 patent/WO2009134694A2/en not_active Ceased
- 2009-04-24 EP EP09739496.9A patent/EP2285900A4/en not_active Withdrawn
- 2009-04-24 US US12/990,510 patent/US8461237B2/en not_active Expired - Fee Related
- 2009-04-24 CN CN2009801235637A patent/CN102066486B/zh not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2009269974A (ja) | 2009-11-19 |
| AU2009241418A1 (en) | 2009-11-05 |
| US20110097585A1 (en) | 2011-04-28 |
| US8461237B2 (en) | 2013-06-11 |
| WO2009134694A2 (en) | 2009-11-05 |
| CN102066486B (zh) | 2013-08-14 |
| WO2009134694A3 (en) | 2009-12-23 |
| CN102066486A (zh) | 2011-05-18 |
| EP2285900A2 (en) | 2011-02-23 |
| EP2285900A4 (en) | 2017-06-14 |
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