CA2582418A1 - Amphiphilic block copolymer-modified epoxy resins and adhesives made therefrom - Google Patents
Amphiphilic block copolymer-modified epoxy resins and adhesives made therefrom Download PDFInfo
- Publication number
- CA2582418A1 CA2582418A1 CA 2582418 CA2582418A CA2582418A1 CA 2582418 A1 CA2582418 A1 CA 2582418A1 CA 2582418 CA2582418 CA 2582418 CA 2582418 A CA2582418 A CA 2582418A CA 2582418 A1 CA2582418 A1 CA 2582418A1
- Authority
- CA
- Canada
- Prior art keywords
- composition
- block
- epoxy resin
- block copolymer
- epoxy
- 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.)
- Abandoned
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 46
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 36
- 229920006332 epoxy adhesive Polymers 0.000 title claims abstract description 12
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical class C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 title description 18
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 128
- 239000000203 mixture Substances 0.000 claims abstract description 116
- 239000003822 epoxy resin Substances 0.000 claims abstract description 106
- 229920001400 block copolymer Polymers 0.000 claims abstract description 97
- 229920000570 polyether Polymers 0.000 claims abstract description 63
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 62
- 229920000469 amphiphilic block copolymer Polymers 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 22
- 239000000178 monomer Substances 0.000 claims abstract description 19
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 239000004840 adhesive resin Substances 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 239000004593 Epoxy Substances 0.000 claims description 40
- -1 polybutylene Polymers 0.000 claims description 35
- 229920001577 copolymer Polymers 0.000 claims description 21
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 229920001519 homopolymer Polymers 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 7
- 239000000945 filler Substances 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229920001748 polybutylene Polymers 0.000 claims description 5
- 229910021485 fumed silica Inorganic materials 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 claims description 2
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 150000001469 hydantoins Chemical class 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- QCGKUFZYSPBMAY-UHFFFAOYSA-N methyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1C(C(=O)OC)CCC2OC21 QCGKUFZYSPBMAY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 229920006305 unsaturated polyester Polymers 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 239000000440 bentonite Substances 0.000 claims 1
- 229910000278 bentonite Inorganic materials 0.000 claims 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 239000008119 colloidal silica Substances 0.000 claims 1
- 239000010445 mica Substances 0.000 claims 1
- 229910052618 mica group Inorganic materials 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 claims 1
- 229920000359 diblock copolymer Polymers 0.000 abstract description 23
- 229920000428 triblock copolymer Polymers 0.000 abstract description 12
- 229920005989 resin Polymers 0.000 description 31
- 239000011347 resin Substances 0.000 description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
- 229920000642 polymer Polymers 0.000 description 15
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000011342 resin composition Substances 0.000 description 12
- 229920001187 thermosetting polymer Polymers 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- 239000000693 micelle Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 229940106691 bisphenol a Drugs 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 238000001338 self-assembly Methods 0.000 description 6
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000012745 toughening agent Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 239000004034 viscosity adjusting agent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 2
- MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920005682 EO-PO block copolymer Polymers 0.000 description 2
- 239000006145 Eagle's minimal essential medium Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 150000001721 carbon Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000013020 final formulation Substances 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 230000000877 morphologic effect Effects 0.000 description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical class C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 1
- JYCBKACCAKPQPJ-UHFFFAOYSA-N 2-(7-oxabicyclo[4.1.0]heptan-4-ylmethyl)hexanedioic acid Chemical compound C1C(CC(CCCC(=O)O)C(O)=O)CCC2OC21 JYCBKACCAKPQPJ-UHFFFAOYSA-N 0.000 description 1
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- ZHNUHDYFZUAESO-OUBTZVSYSA-N aminoformaldehyde Chemical compound N[13CH]=O ZHNUHDYFZUAESO-OUBTZVSYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000007630 basic procedure Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000010960 cold rolled steel Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- PQANGXXSEABURG-UHFFFAOYSA-N cyclohex-2-en-1-ol Chemical class OC1CCCC=C1 PQANGXXSEABURG-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920006030 multiblock copolymer Polymers 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- GAGSAAHZRBTRGD-UHFFFAOYSA-N oxirane;oxolane Chemical compound C1CO1.C1CCOC1 GAGSAAHZRBTRGD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000977 poly(butadiene-b-ethylene oxide) Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
- C09J171/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/126—Copolymers block
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
- C08L2666/22—Macromolecular compounds not provided for in C08L2666/16 - C08L2666/20
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- 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]
- Y10T428/31511—Of epoxy ether
- Y10T428/31515—As intermediate layer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62661904P | 2004-11-10 | 2004-11-10 | |
| US60/626,619 | 2004-11-10 | ||
| PCT/US2005/039962 WO2006052726A1 (en) | 2004-11-10 | 2005-11-02 | Amphiphilic block copolymer-modified epoxy resins and adhesives made therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2582418A1 true CA2582418A1 (en) | 2006-05-18 |
Family
ID=35768596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2582418 Abandoned CA2582418A1 (en) | 2004-11-10 | 2005-11-02 | Amphiphilic block copolymer-modified epoxy resins and adhesives made therefrom |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7820760B2 (https=) |
| EP (1) | EP1812512B1 (https=) |
| JP (1) | JP2008519885A (https=) |
| KR (1) | KR101226379B1 (https=) |
| CN (2) | CN101864261B (https=) |
| AT (1) | ATE454428T1 (https=) |
| BR (1) | BRPI0516699A (https=) |
| CA (1) | CA2582418A1 (https=) |
| DE (1) | DE602005018806D1 (https=) |
| ES (1) | ES2335600T3 (https=) |
| MX (1) | MX2007005599A (https=) |
| NO (1) | NO20071728L (https=) |
| RU (1) | RU2389742C2 (https=) |
| TW (1) | TWI431088B (https=) |
| WO (1) | WO2006052726A1 (https=) |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2006138618A (ru) * | 2004-04-02 | 2008-05-10 | Дау Глобал Текнолоджиз Инк. (Us) | Модифицированные амфифильным блок-сополимером термоотверждающиеся смолы с повышенной ударной вязкостью |
| EP1814947B1 (en) * | 2004-11-10 | 2009-12-30 | Dow Global Technologies Inc. | Amphiphilic block copolymer-toughened epoxy resins |
| DE102005042916A1 (de) * | 2005-09-08 | 2007-03-22 | Degussa Ag | Stapel aus abwechselnd übereinander gestapelten und fixierten Separatoren und Elektroden für Li-Akkumulatoren |
| EP1972646A1 (de) | 2007-03-20 | 2008-09-24 | Sika Technology AG | Epoxidgruppen terminierte Polymer, deren Zusammensetzungen und deren Verwendung als Schlagzähigkeitsmodifikatoren |
| KR20150063590A (ko) * | 2007-08-02 | 2015-06-09 | 다우 글로벌 테크놀로지스 엘엘씨 | 열경화성 중합체의 성능을 개선시키기 위한 양친매성 블록 공중합체 및 무기 나노충진제 |
| EP2229416B1 (en) | 2008-01-08 | 2018-04-04 | Dow Global Technologies LLC | High tg epoxy systems for composite application |
| EP2110397A1 (de) | 2008-04-16 | 2009-10-21 | Sika Technology AG | Auf amphiphilen Block-Copolymer basierendes Polyurethan-Polymer und dessen Verwendung als Schlagzähigkeitsmodifikator |
| EP2113525A1 (de) | 2008-04-30 | 2009-11-04 | Sika Technology AG | Aktivator für Epoxidharzzusammensetzungen |
| JP5687187B2 (ja) | 2008-04-30 | 2015-03-18 | シーカ・テクノロジー・アーゲー | エポキシ樹脂組成物のための活性剤 |
| US8829101B2 (en) | 2008-05-16 | 2014-09-09 | Dow Global Technologies Llc | Windmill propeller blade and method of making same |
| EP2128182A1 (de) | 2008-05-28 | 2009-12-02 | Sika Technology AG | Hitzehärtende Epoxidharzzusammensetzung enthaltend einen Beschleuniger mit Heteroatomen |
| ATE461953T1 (de) | 2008-07-17 | 2010-04-15 | Sika Technology Ag | Haftvermittlerverbindungen für beölten stahl |
| EP2145924A1 (de) | 2008-07-18 | 2010-01-20 | Sika Technology AG | Auf amphiphilen Block-Copolymer basierende Reaktionsprodukte und deren Verwendung als Schlagzähigkeitsmodifikator |
| ATE468344T1 (de) | 2008-08-27 | 2010-06-15 | Sika Technology Ag | Silan-/harnstoff-verbindung als hitzeaktivierbarer härter für epoxidharzzusammensetzungen |
| EP2182025B1 (de) | 2008-10-31 | 2010-10-06 | Sika Technology AG | Hitzehärtende Epoxidharzzusammensetzungen einsetzbar als Rohbauklebstoff oder Strukturschaum |
| CA2750703A1 (en) | 2009-02-24 | 2010-09-02 | Gary A. Hunter | Curable epoxy resin compositions and cured products therefrom |
| CN105131525A (zh) * | 2009-03-09 | 2015-12-09 | 陶氏环球技术有限责任公司 | 含有两亲型嵌段共聚物和多元醇的组合的可热固化组合物及其热固产品 |
| PL2406316T3 (pl) | 2009-03-09 | 2018-04-30 | Dow Global Technologies Llc | Termoutwardzalna kompozycja zawierająca kombinację amfifilowego kopolimeru blokowego i poliolu oraz utwardzony termicznie produkt z niej wytworzony |
| EP2365046A1 (de) | 2010-03-02 | 2011-09-14 | Sika Technology AG | Schlagzäher bei Raumtemperatur härtender zwei-komponentiger Strukturklebstoff |
| EP2365011A1 (de) | 2010-03-02 | 2011-09-14 | Sika Technology AG | Aminogruppen - terminierter Schlagzähigkeitsmodifikator und dessen Verwendungen in Epoxidharzzusammensetzungen |
| EP2552991A1 (en) * | 2010-03-31 | 2013-02-06 | Dow Global Technologies LLC | Curable compositions |
| EP2436712A1 (de) | 2010-10-01 | 2012-04-04 | Sika Technology AG | Schlagzähigkeitsmodifikatoren für Epoxidharzzusammensetzungen |
| BR112013015065A2 (pt) * | 2010-12-28 | 2016-08-09 | Saint Gobain Abrasives Inc | roda de esmerilhamento ligada por ligante robusto |
| CA2817987A1 (en) | 2011-02-24 | 2012-08-30 | Felix N. Nguyen | Reinforced interphase and bonded structures thereof |
| US20120279762A1 (en) * | 2011-05-03 | 2012-11-08 | Industry-Academic Cooperation Foundation, Yonsei University | Composition for forming stretchable conductive pattern, method of producing the stretchable conductive pattern using the composition, and electronic device including stretchable conductive electrode |
| GB201113196D0 (en) | 2011-08-01 | 2011-09-14 | Cytec Tech Corp | Thermoset resin compositions with increased toughness |
| WO2013074265A1 (en) | 2011-11-14 | 2013-05-23 | Henkel Corporation | Adhesive compositions |
| WO2013095908A2 (en) | 2011-12-20 | 2013-06-27 | Dow Global Technologies Llc | Epoxy resin composites |
| US9263360B2 (en) * | 2012-07-06 | 2016-02-16 | Henkel IP & Holding GmbH | Liquid compression molding encapsulants |
| ITMI20121330A1 (it) | 2012-07-31 | 2014-02-01 | Dow Global Technologies Llc | Metodo per la preparazione di pannelli isolanti espansi resistenti alla fiamma |
| KR102173954B1 (ko) * | 2012-08-13 | 2020-11-04 | 헨켈 아이피 앤드 홀딩 게엠베하 | 액체 압축 성형 캡슐화제 |
| CN104837931B (zh) * | 2012-12-20 | 2017-12-01 | 陶氏环球技术有限责任公司 | 无线通信塔用的聚合物复合材料组件 |
| JP6384487B2 (ja) | 2012-12-27 | 2018-09-05 | 東レ株式会社 | 硬質界面相を有する繊維強化ポリマー複合材料 |
| KR101617387B1 (ko) * | 2013-02-26 | 2016-05-02 | 주식회사 엘지화학 | 코팅 조성물 및 이로부터 제조되는 플라스틱 필름 |
| KR102251170B1 (ko) | 2013-07-22 | 2021-05-13 | 헨켈 아이피 앤드 홀딩 게엠베하 | 웨이퍼의 압축 성형시의 웨이퍼 휨을 제어하는 방법 및 그에 유용한 물품 |
| RU2544691C1 (ru) * | 2013-10-15 | 2015-03-20 | Федеральное государственное унитарное предприятие "Научно-исследовательский институт химии и технологии полимеров имени академика В.А. Каргина с опытным заводом" (ФГУП "НИИ полимеров") | Термоотверждаемая акриловая клеевая композиция |
| FR3014444B1 (fr) * | 2013-12-10 | 2017-03-03 | Commissariat Energie Atomique | Utilisation d'un copolymere a blocs amphiphile pour l'obtention d'un materiau presentant des proprietes de resistance a l'humidite ameliorees |
| US9245815B2 (en) * | 2014-04-29 | 2016-01-26 | Intel Corporation | Underfill material including block copolymer to tune coefficient of thermal expansion and tensile modulus |
| US10208157B2 (en) | 2014-09-11 | 2019-02-19 | Blue Cube Ip Llc | Ester resins |
| KR102481399B1 (ko) * | 2014-11-11 | 2022-12-27 | 다우 글로벌 테크놀로지스 엘엘씨 | 유리 구체를 갖는 접착제 조성물 |
| EP3240830B1 (en) * | 2014-12-31 | 2020-09-30 | Dow Global Technologies LLC | Crash durable epoxy adhesive compositions having improved low-temperature impact resistance and wash off resistance |
| WO2017040883A1 (en) | 2015-09-04 | 2017-03-09 | Carbon, Inc. | Cyanate ester dual cure resins for additive manufacturing |
| WO2017044381A1 (en) | 2015-09-09 | 2017-03-16 | Carbon3D, Inc. | Epoxy dual cure resins for additive manufacturing |
| WO2017055920A1 (en) | 2015-09-28 | 2017-04-06 | Toray Industries, Inc. | Prepreg with variable cure rate resin compositions |
| WO2017079502A1 (en) | 2015-11-05 | 2017-05-11 | Carbon, Inc. | Silicone dual cure resins for additive manufacturing |
| WO2017112653A1 (en) | 2015-12-22 | 2017-06-29 | Carbon, Inc. | Dual precursor resin systems for additive manufacturing with dual cure resins |
| WO2017112483A2 (en) | 2015-12-22 | 2017-06-29 | Carbon, Inc. | Accelerants for additive manufacturing with dual cure resins |
| WO2017112571A1 (en) | 2015-12-22 | 2017-06-29 | Carbon, Inc. | Dual cure additive manufacturing of rigid intermediates that generate semi-rigid, flexible, or elastic final products |
| WO2017112521A1 (en) | 2015-12-22 | 2017-06-29 | Carbon, Inc. | Production of flexible products by additive manufacturing with dual cure resins |
| WO2017112751A1 (en) | 2015-12-22 | 2017-06-29 | Carbon, Inc. | Blocked silicone dual cure resins for additive manufacturing |
| CN108475008B (zh) | 2015-12-22 | 2020-11-06 | 卡本有限公司 | 一种形成三维物体的方法 |
| CN110072915A (zh) | 2016-10-28 | 2019-07-30 | 陶氏环球技术有限责任公司 | 具有改善的低温耐冲击性的耐碰撞环氧粘合剂 |
| WO2018094131A1 (en) | 2016-11-21 | 2018-05-24 | Carbon, Inc. | Method of making three-dimensional object by delivering reactive component for subsequent cure |
| CN106613280A (zh) * | 2017-01-11 | 2017-05-10 | 杭州花泽园艺工程有限公司 | 一种中绿篱植物的种植方法 |
| JP7067140B2 (ja) * | 2017-03-29 | 2022-05-16 | 味の素株式会社 | 樹脂組成物 |
| US10239255B2 (en) | 2017-04-11 | 2019-03-26 | Molecule Corp | Fabrication of solid materials or films from a polymerizable liquid |
| TWI768032B (zh) | 2017-04-21 | 2022-06-21 | 德商漢高智慧財產控股公司 | 黏著劑組合物 |
| EP3612609B1 (en) | 2017-04-21 | 2022-12-28 | Henkel AG & Co. KGaA | Adhesive compositions |
| US11135766B2 (en) | 2017-06-29 | 2021-10-05 | Carbon, Inc. | Products containing nylon 6 produced by stereolithography and methods of making the same |
| CN107619578A (zh) * | 2017-10-25 | 2018-01-23 | 山东非金属材料研究所 | 一种vartm用喷胶及其制备方法 |
| CN109721947A (zh) | 2017-10-27 | 2019-05-07 | 财团法人工业技术研究院 | 环氧树脂组合物 |
| WO2020131675A1 (en) | 2018-12-21 | 2020-06-25 | Carbon, Inc. | Energy absorbing dual cure polyurethane elastomers for additive manufacturing |
| CN111040700A (zh) * | 2019-12-28 | 2020-04-21 | 长沙索康新材料科技有限公司 | 一种高强度混凝土修补用环氧胶泥 |
| WO2021173785A1 (en) | 2020-02-28 | 2021-09-02 | Carbon, Inc. | One part moisture curable resins for additive manufacturing |
| US20230078824A1 (en) | 2020-02-28 | 2023-03-16 | Carbon, Inc. | Methods of making a three-dimensional object |
| WO2021202655A1 (en) | 2020-04-03 | 2021-10-07 | Carbon, Inc. | Resins and methods for additive manufacturing of energy absorbing three-dimensional objects |
| US11655329B2 (en) | 2020-04-24 | 2023-05-23 | Carbon, Inc. | Delayed action catalysts for dual cure additive manufacturing resins |
| US20230129561A1 (en) | 2020-04-28 | 2023-04-27 | Carbon, Inc. | Methods of making a three-dimensional object |
| CN112724898A (zh) * | 2020-12-25 | 2021-04-30 | 深圳市南科康达科技有限公司 | 一种环氧树脂组合物及其制备方法和应用 |
| WO2022256635A1 (en) | 2021-06-03 | 2022-12-08 | Carbon, Inc. | Methods for the rapid production of blocked prepolymers |
| US11884000B2 (en) | 2021-08-27 | 2024-01-30 | Carbon, Inc. | One part, catalyst containing, moisture curable dual cure resins for additive manufacturing |
| CN115322523B (zh) * | 2022-08-23 | 2023-07-21 | 成都飞机工业（集团）有限责任公司 | 含两亲性液晶嵌段共聚物的环氧树脂组合物及其制备方法 |
| CN119875091B (zh) * | 2025-03-28 | 2025-06-27 | 宁波堇山新材料有限公司 | 一种改性剂和不饱和聚酯树脂固化物及其制备方法和在图像捕捉装置罩面上的应用 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3948698A (en) | 1967-09-06 | 1976-04-06 | Hercules Incorporated | Solid propellant compositions having epoxy cured, carboxy-terminated rubber binder |
| US3804735A (en) | 1972-04-10 | 1974-04-16 | Continental Can Co | Photopolymerizable compositions prepared from beta-hydroxy esters and polyitaconates |
| US3892819A (en) | 1973-03-21 | 1975-07-01 | Dow Chemical Co | Impact resistant vinyl ester resin and process for making same |
| DE2349979A1 (de) | 1973-10-04 | 1975-04-17 | Bayer Ag | Uv-licht-haertende massen hoher reaktivitaet |
| US4119609A (en) | 1977-03-28 | 1978-10-10 | Shell Oil Company | Curable epoxy-carboxylic acid adducts |
| US4431782A (en) | 1981-07-27 | 1984-02-14 | The Dow Chemical Company | Process for the preparation of radiation-curable, water-thinnable vinyl ester resins |
| US5278257A (en) | 1987-08-26 | 1994-01-11 | Ciba-Geigy Corporation | Phenol-terminated polyurethane or polyurea(urethane) with epoxy resin |
| EP0384896A1 (de) * | 1989-02-24 | 1990-08-29 | Ciba-Geigy Ag | Zähe Epoxidgiessharze |
| TW346498B (en) * | 1994-10-11 | 1998-12-01 | Shell Int Research | Epoxidized monohydroxylated rubber toughening modifiers for epoxy resins |
| RU2092505C1 (ru) * | 1995-03-20 | 1997-10-10 | Акционерное общество Научно-производственное объединение "Стеклопластик" | Способ получения эпоксидной дисперсии |
| CN1056402C (zh) * | 1996-01-31 | 2000-09-13 | 中国科学院化学研究所 | 一种抗流淌糊状环氧胶粘剂 |
| JP3620921B2 (ja) | 1996-06-06 | 2005-02-16 | 株式会社タイルメント | 硬化性エポキシ樹脂系接着剤 |
| US20040181013A1 (en) | 1998-10-06 | 2004-09-16 | Henkel Teroson Gmbh | Impact resistant epoxide resin compositions |
| CN1250665C (zh) | 2000-04-10 | 2006-04-12 | 汉高两合股份公司 | 抗冲击环氧树脂组合物 |
| FR2809741B1 (fr) * | 2000-05-31 | 2002-08-16 | Atofina | Materiaux thermodurs a tenue au choc amelioree |
| JPWO2002055625A1 (ja) * | 2001-01-15 | 2004-05-13 | 積水化学工業株式会社 | 光反応性ホットメルト接着剤組成物 |
| US7041355B2 (en) | 2001-11-29 | 2006-05-09 | Dow Global Technologies Inc. | Structural reinforcement parts for automotive assembly |
| JP2003183605A (ja) * | 2001-12-19 | 2003-07-03 | Sekisui Chem Co Ltd | 光反応性ホットメルト接着シート |
| JP3820147B2 (ja) * | 2001-12-26 | 2006-09-13 | 積水化学工業株式会社 | 光硬化可能組成物 |
| US20030192643A1 (en) | 2002-03-15 | 2003-10-16 | Rainer Schoenfeld | Epoxy adhesive having improved impact resistance |
| KR100931762B1 (ko) | 2002-04-15 | 2009-12-14 | 다우 글로벌 테크놀로지스 인크. | 발포체 제품 및 이를 사용한 발포체 충전 차량 중공 부재 형성 방법 |
| US7169344B2 (en) | 2002-04-26 | 2007-01-30 | L&L Products, Inc. | Method of reinforcing at least a portion of a structure |
| JP2004182935A (ja) * | 2002-12-05 | 2004-07-02 | Ricoh Co Ltd | 導電性接着剤 |
| EP1431325A1 (de) | 2002-12-17 | 2004-06-23 | Sika Technology AG | Hitze-härtbare Epoxidharzzusammensetzung mit verbesserter Tieftemperatur-Schlagzähigkeit |
| GB0300159D0 (en) | 2003-01-06 | 2003-02-05 | L & L Products Inc | Improved reinforcing members |
-
2005
- 2005-11-02 KR KR1020077010528A patent/KR101226379B1/ko not_active Expired - Fee Related
- 2005-11-02 ES ES05818168T patent/ES2335600T3/es not_active Expired - Lifetime
- 2005-11-02 AT AT05818168T patent/ATE454428T1/de not_active IP Right Cessation
- 2005-11-02 EP EP20050818168 patent/EP1812512B1/en not_active Expired - Lifetime
- 2005-11-02 DE DE200560018806 patent/DE602005018806D1/de not_active Expired - Lifetime
- 2005-11-02 MX MX2007005599A patent/MX2007005599A/es unknown
- 2005-11-02 US US11/663,805 patent/US7820760B2/en active Active
- 2005-11-02 WO PCT/US2005/039962 patent/WO2006052726A1/en not_active Ceased
- 2005-11-02 CA CA 2582418 patent/CA2582418A1/en not_active Abandoned
- 2005-11-02 BR BRPI0516699-3A patent/BRPI0516699A/pt not_active Application Discontinuation
- 2005-11-02 CN CN2010101986039A patent/CN101864261B/zh not_active Expired - Lifetime
- 2005-11-02 RU RU2007121649A patent/RU2389742C2/ru not_active IP Right Cessation
- 2005-11-02 CN CN2005800385357A patent/CN101056934B/zh not_active Expired - Lifetime
- 2005-11-02 JP JP2007541251A patent/JP2008519885A/ja active Pending
- 2005-11-09 TW TW94139241A patent/TWI431088B/zh not_active IP Right Cessation
-
2007
- 2007-04-02 NO NO20071728A patent/NO20071728L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1812512A1 (en) | 2007-08-01 |
| CN101056934B (zh) | 2010-09-29 |
| RU2007121649A (ru) | 2008-12-20 |
| CN101864261A (zh) | 2010-10-20 |
| JP2008519885A (ja) | 2008-06-12 |
| TWI431088B (zh) | 2014-03-21 |
| KR101226379B1 (ko) | 2013-01-24 |
| DE602005018806D1 (de) | 2010-02-25 |
| RU2389742C2 (ru) | 2010-05-20 |
| CN101864261B (zh) | 2012-09-05 |
| BRPI0516699A (pt) | 2008-09-16 |
| TW200624530A (en) | 2006-07-16 |
| MX2007005599A (es) | 2007-05-23 |
| US7820760B2 (en) | 2010-10-26 |
| CN101056934A (zh) | 2007-10-17 |
| ES2335600T3 (es) | 2010-03-30 |
| US20090123759A1 (en) | 2009-05-14 |
| WO2006052726A1 (en) | 2006-05-18 |
| EP1812512B1 (en) | 2010-01-06 |
| NO20071728L (no) | 2007-08-08 |
| ATE454428T1 (de) | 2010-01-15 |
| KR20070084112A (ko) | 2007-08-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7820760B2 (en) | Amphiphilic block copolymer-modified epoxy resins and adhesives made therefrom | |
| EP1812513B1 (en) | Amphiphilic block copolymer-toughened epoxy resins and powder coatings made therefrom | |
| EP1814947B1 (en) | Amphiphilic block copolymer-toughened epoxy resins | |
| EP1812511B1 (en) | Amphiphilic block copolymer-toughened epoxy resins and ambient cure high-solids coatings made therefrom | |
| HK1116814A (en) | Amphiphilic block copolymer-toughened epoxy resins and powder coatings made therefrom | |
| HK1112930A1 (en) | Amphiphilic block copolymer-toughened epoxy resins and electrical laminates made therefrom | |
| HK1112930B (en) | Amphiphilic block copolymer-toughened epoxy resins and electrical laminates made therefrom |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140806 |