ES2690653T3 - Composiciones curables reforzadas - Google Patents
Composiciones curables reforzadas Download PDFInfo
- Publication number
- ES2690653T3 ES2690653T3 ES09789826.6T ES09789826T ES2690653T3 ES 2690653 T3 ES2690653 T3 ES 2690653T3 ES 09789826 T ES09789826 T ES 09789826T ES 2690653 T3 ES2690653 T3 ES 2690653T3
- Authority
- ES
- Spain
- Prior art keywords
- nanoparticles
- rubber
- curable composition
- grams
- silica
- 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.)
- Active
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- 239000000203 mixture Substances 0.000 title claims abstract description 110
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 229
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 105
- 239000002105 nanoparticle Substances 0.000 claims abstract description 96
- 229920005989 resin Polymers 0.000 claims abstract description 87
- 239000011347 resin Substances 0.000 claims abstract description 87
- 229920001971 elastomer Polymers 0.000 claims abstract description 79
- 239000005060 rubber Substances 0.000 claims abstract description 79
- 239000011258 core-shell material Substances 0.000 claims abstract description 26
- 239000012756 surface treatment agent Substances 0.000 claims abstract description 11
- 238000004627 transmission electron microscopy Methods 0.000 claims abstract description 6
- 239000011164 primary particle Substances 0.000 claims abstract description 4
- 239000004593 Epoxy Substances 0.000 claims description 24
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 claims description 19
- 239000002245 particle Substances 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 230000009477 glass transition Effects 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 8
- 229920000428 triblock copolymer Polymers 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 6
- 239000002131 composite material Substances 0.000 claims description 6
- 229920001400 block copolymer Polymers 0.000 claims description 5
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000011159 matrix material Substances 0.000 claims description 3
- UIMKIFAISLCAGY-UHFFFAOYSA-N 2,2-dimethoxy-4,5-dihydro-3h-1,2-benzoxasilepine Chemical compound O1[Si](OC)(OC)CCCC2=CC=CC=C21 UIMKIFAISLCAGY-UHFFFAOYSA-N 0.000 claims description 2
- 229920006243 acrylic copolymer Polymers 0.000 claims description 2
- 229920000800 acrylic rubber Polymers 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 229920003244 diene elastomer Polymers 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001282 organosilanes Chemical class 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 229920006249 styrenic copolymer Polymers 0.000 claims description 2
- UBMUZYGBAGFCDF-UHFFFAOYSA-N trimethoxy(2-phenylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=C1 UBMUZYGBAGFCDF-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims 2
- 239000000945 filler Substances 0.000 claims 1
- 229920000647 polyepoxide Polymers 0.000 description 44
- 239000003822 epoxy resin Substances 0.000 description 38
- 239000000523 sample Substances 0.000 description 37
- 239000000243 solution Substances 0.000 description 33
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 31
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000003039 volatile agent Substances 0.000 description 20
- 239000011342 resin composition Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 10
- 239000004848 polyfunctional curative Substances 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000001723 curing Methods 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- -1 e.g. eg Polymers 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
- RJSIOBPBENPMRZ-ZJJOJAIXSA-N (2s)-n-[(4s)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-5-hydroxypentyl]-2-[[2-(4-methoxyphenyl)acetyl]amino]-3-naphthalen-1-ylpropanamide Chemical compound C1=CC(OC)=CC=C1CC(=O)N[C@H](C(=O)NCCC[C@@H](CO)N(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)CC1=CC=CC2=CC=CC=C12 RJSIOBPBENPMRZ-ZJJOJAIXSA-N 0.000 description 5
- DZRJLJPPUJADOO-UHFFFAOYSA-N chaetomin Natural products CN1C(=O)C2(Cc3cn(C)c4ccccc34)SSC1(CO)C(=O)N2C56CC78SSC(CO)(N(C)C7=O)C(=O)N8C5Nc9ccccc69 DZRJLJPPUJADOO-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- HGXVKAPCSIXGAK-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine;4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N.CCC1=CC(C)=C(N)C(CC)=C1N HGXVKAPCSIXGAK-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CCPHAMSKHBDMDS-UHFFFAOYSA-N Chetoseminudin B Natural products C=1NC2=CC=CC=C2C=1CC1(SC)NC(=O)C(CO)(SC)N(C)C1=O CCPHAMSKHBDMDS-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- DIUIQJFZKRAGBZ-UHFFFAOYSA-N chetoseminudin A Natural products O=C1C(SSS2)(CO)N(C)C(=O)C32CC2(N4C5=CC=CC=C5C(CC56C(N(C)C(CO)(SS5)C(=O)N6C)=O)=C4)C4=CC=CC=C4NC2N31 DIUIQJFZKRAGBZ-UHFFFAOYSA-N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 2
- RQEOBXYYEPMCPJ-UHFFFAOYSA-N 4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N RQEOBXYYEPMCPJ-UHFFFAOYSA-N 0.000 description 2
- CYSPWCARDHRYJX-UHFFFAOYSA-N 9h-fluoren-1-amine Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2N CYSPWCARDHRYJX-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- UIDDPPKZYZTEGS-UHFFFAOYSA-N 3-(2-ethyl-4-methylimidazol-1-yl)propanenitrile Chemical compound CCC1=NC(C)=CN1CCC#N UIDDPPKZYZTEGS-UHFFFAOYSA-N 0.000 description 1
- CPHGOBGXZQKCKI-UHFFFAOYSA-N 4,5-diphenyl-1h-imidazole Chemical compound N1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CPHGOBGXZQKCKI-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- FKBMTBAXDISZGN-UHFFFAOYSA-N 5-methyl-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1C(C)CCC2C(=O)OC(=O)C12 FKBMTBAXDISZGN-UHFFFAOYSA-N 0.000 description 1
- 229920003319 Araldite® Polymers 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000013006 addition curing Methods 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical class C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 1
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 1
- 239000004126 brilliant black BN Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000004643 cyanate ester Substances 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- 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
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- 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
- C08L51/003—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 macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
- Wire Bonding (AREA)
- Reinforced Plastic Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6179508P | 2008-06-16 | 2008-06-16 | |
| US61795P | 2008-06-16 | ||
| PCT/US2009/047465 WO2010005710A1 (en) | 2008-06-16 | 2009-06-16 | Toughened curable compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2690653T3 true ES2690653T3 (es) | 2018-11-21 |
Family
ID=41182192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09789826.6T Active ES2690653T3 (es) | 2008-06-16 | 2009-06-16 | Composiciones curables reforzadas |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20110097212A1 (enExample) |
| EP (1) | EP2294119B1 (enExample) |
| JP (3) | JP2011525207A (enExample) |
| KR (1) | KR20110039257A (enExample) |
| CN (1) | CN102112536B (enExample) |
| ES (1) | ES2690653T3 (enExample) |
| WO (1) | WO2010005710A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8309633B2 (en) * | 2008-07-17 | 2012-11-13 | Henkel Ireland Ltd. | Low temperature, cationically curable compositions with improved cure speed and toughness |
| EP2435178B1 (en) | 2009-05-26 | 2020-08-12 | 3M Innovative Properties Company | Process for making filled resins |
| CN102741338B (zh) | 2010-02-11 | 2015-04-15 | 3M创新有限公司 | 包括分散的多峰表面改性纳米粒子的树脂体系 |
| CN102947405B (zh) | 2010-04-20 | 2015-07-01 | 3M创新有限公司 | 包含聚合表面改性的纳米粒子的压敏粘合剂 |
| JP6026095B2 (ja) * | 2011-10-31 | 2016-11-16 | 太陽インキ製造株式会社 | 熱硬化性樹脂組成物及びその硬化物、並びにそれを用いたプリント配線板 |
| US10442914B2 (en) | 2013-08-13 | 2019-10-15 | 3M Innovative Properties Company | Nanocomposites containing silica nanoparticles and dispersant, composites, articles, and methods of making same |
| WO2015102911A1 (en) * | 2013-12-30 | 2015-07-09 | Dow Global Technologies Llc | Toughening agents for epoxy systems |
| CN103899571A (zh) * | 2014-03-17 | 2014-07-02 | 安徽华瑞塑业有限公司 | 独立式轴流泵叶片 |
| DE102014213327A1 (de) * | 2014-07-09 | 2016-01-14 | MTU Aero Engines AG | Anti-fouling-Schicht für Verdichterschaufeln |
| CN107108857B (zh) * | 2014-12-18 | 2020-07-17 | 塞特工业公司 | 适用于液体树脂灌注的改性树脂体系 |
| CN107406575B (zh) * | 2015-02-27 | 2020-01-14 | 3M创新有限公司 | 两部分结构化粘合剂 |
| JP6956388B2 (ja) * | 2016-04-19 | 2021-11-02 | パナソニックＩｐマネジメント株式会社 | プリプレグ、金属張積層板及びプリント配線板 |
| WO2017195902A1 (ja) | 2016-05-13 | 2017-11-16 | 日立化成株式会社 | 樹脂組成物、プリプレグ、樹脂付き金属箔、積層板、プリント配線板及び樹脂組成物の製造方法 |
| WO2018085040A1 (en) | 2016-11-07 | 2018-05-11 | 3M Innovative Properties Company | Curable resin including nanoparticles including surface-bonded hydrophobically-modifying alkyl groups |
| WO2019000375A1 (en) * | 2017-06-30 | 2019-01-03 | Henkel Ag & Co. Kgaa | INORGANIC NANOPARTICLES WITH MODIFIED SURFACE AND USE THEREOF |
| CN107501867A (zh) * | 2017-09-21 | 2017-12-22 | 上海稳优实业有限公司 | 固态颗粒增强环氧树脂及其制备方法 |
| CN109517344B (zh) * | 2018-12-29 | 2021-03-16 | 江苏恒神股份有限公司 | 一种高模量高韧性环氧树脂 |
| CN113278395B (zh) * | 2021-04-12 | 2022-03-18 | 广东博汇新材料科技股份有限公司 | 一种预定型喷胶组合物及其制备方法 |
| CN115157809B (zh) * | 2022-06-09 | 2023-04-07 | 科顺防水科技股份有限公司 | 一种预铺防水卷材及其制备方法 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4684678A (en) * | 1985-05-30 | 1987-08-04 | Minnesota Mining And Manufacturing Company | Epoxy resin curing agent, process, and composition |
| JP2717229B2 (ja) * | 1988-06-21 | 1998-02-18 | 旭化成工業株式会社 | 樹脂補強用ゴム粒子及び補強樹脂組成物 |
| US5290857A (en) * | 1991-09-04 | 1994-03-01 | Nippon Zeon Co., Ltd. | Epoxy resin adhesive composition |
| JP2652093B2 (ja) * | 1991-09-12 | 1997-09-10 | 富士写真フイルム株式会社 | 感光性組成物 |
| JP3655646B2 (ja) * | 1993-05-24 | 2005-06-02 | 日産自動車株式会社 | エポキシ樹脂用接着補強剤及び該補強剤を含有する自動車用エポキシ樹脂系構造接着性組成物 |
| US5648407A (en) * | 1995-05-16 | 1997-07-15 | Minnesota Mining And Manufacturing Company | Curable resin sols and fiber-reinforced composites derived therefrom |
| JP4319332B2 (ja) * | 2000-06-29 | 2009-08-26 | 株式会社東芝 | 電気絶縁材料およびその製造方法 |
| US6800371B2 (en) * | 2001-03-07 | 2004-10-05 | 3M Innovative Properties Company | Adhesives and adhesive compositions containing thioether groups |
| JP2003012320A (ja) * | 2001-06-28 | 2003-01-15 | Catalysts & Chem Ind Co Ltd | シリカ系無機化合物オルガノゾル |
| US20030111519A1 (en) * | 2001-09-04 | 2003-06-19 | 3M Innovative Properties Company | Fluxing compositions |
| US6893736B2 (en) * | 2001-11-19 | 2005-05-17 | Henkel Corporation | Thermosetting resin compositions useful as underfill sealants |
| CN100521869C (zh) * | 2002-05-23 | 2009-07-29 | 3M创新有限公司 | 纳米颗粒填充的底层填料 |
| JP2004083651A (ja) * | 2002-08-23 | 2004-03-18 | Toray Ind Inc | 吸湿性ポリエステル組成物およびポリエステル繊維 |
| US6811823B2 (en) * | 2002-09-13 | 2004-11-02 | Dow Corning Corporation | Hydrophobing silica with organosilicon compounds and blends thereof |
| US7056978B2 (en) * | 2002-11-06 | 2006-06-06 | National Starch And Chemical Investment Holding Corporation | Toughened epoxy-anhydride no-flow underfill encapsulant |
| US20050048291A1 (en) * | 2003-08-14 | 2005-03-03 | General Electric Company | Nano-filled composite materials with exceptionally high glass transition temperature |
| DE50304047D1 (de) * | 2003-03-11 | 2006-08-10 | Hanse Chemie Ag | Polymere Epoxidharz-Zusammensetzung |
| EP1457509B1 (de) * | 2003-03-11 | 2006-06-28 | hanse chemie AG | Polymere Epoxidharz-Zusammensetzung |
| JP4066870B2 (ja) * | 2003-04-10 | 2008-03-26 | Ｊｓｒ株式会社 | 液状硬化性組成物、硬化膜及び帯電防止用積層体 |
| US7666938B2 (en) * | 2004-12-03 | 2010-02-23 | Henkel Corporation | Nanoparticle silica filled benzoxazine compositions |
| US20060199301A1 (en) * | 2005-03-07 | 2006-09-07 | Basheer Rafil A | Methods of making a curable composition having low coefficient of thermal expansion and an integrated circuit and a curable composition and integrated circuit made there from |
| CA2620028C (en) * | 2005-08-24 | 2014-01-28 | Henkel Kommanditgesellschaft Auf Aktien | Epoxy compositions having improved impact resistance |
| TWI410442B (zh) * | 2005-11-29 | 2013-10-01 | Ajinomoto Kk | A resin composition for an insulating layer of a multilayer printed circuit board |
| JP4983228B2 (ja) * | 2005-11-29 | 2012-07-25 | 味の素株式会社 | 多層プリント配線板の絶縁層用樹脂組成物 |
| JP2008031193A (ja) * | 2006-07-26 | 2008-02-14 | Toray Ind Inc | エポキシ樹脂組成物、プリプレグ、繊維強化複合材料 |
| JP4905668B2 (ja) * | 2006-09-15 | 2012-03-28 | 信越化学工業株式会社 | 半導体封止用液状エポキシ樹脂組成物及び半導体装置 |
-
2009
- 2009-06-16 WO PCT/US2009/047465 patent/WO2010005710A1/en not_active Ceased
- 2009-06-16 CN CN200980129889.0A patent/CN102112536B/zh active Active
- 2009-06-16 JP JP2011514739A patent/JP2011525207A/ja not_active Withdrawn
- 2009-06-16 EP EP09789826.6A patent/EP2294119B1/en active Active
- 2009-06-16 ES ES09789826.6T patent/ES2690653T3/es active Active
- 2009-06-16 US US12/997,939 patent/US20110097212A1/en not_active Abandoned
- 2009-06-16 KR KR1020117000672A patent/KR20110039257A/ko not_active Ceased
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2014
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2016
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2010005710A1 (en) | 2010-01-14 |
| US20110097212A1 (en) | 2011-04-28 |
| EP2294119A1 (en) | 2011-03-16 |
| EP2294119B1 (en) | 2018-08-01 |
| JP2014218675A (ja) | 2014-11-20 |
| KR20110039257A (ko) | 2011-04-15 |
| JP2011525207A (ja) | 2011-09-15 |
| CN102112536B (zh) | 2015-06-24 |
| JP2016199767A (ja) | 2016-12-01 |
| JP6437966B2 (ja) | 2018-12-12 |
| CN102112536A (zh) | 2011-06-29 |
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