CA2582341A1 - Amphiphilic block copolymer-toughened epoxy resins and powder coatings made therefrom - Google Patents
Amphiphilic block copolymer-toughened epoxy resins and powder coatings made therefrom Download PDFInfo
- Publication number
- CA2582341A1 CA2582341A1 CA 2582341 CA2582341A CA2582341A1 CA 2582341 A1 CA2582341 A1 CA 2582341A1 CA 2582341 CA2582341 CA 2582341 CA 2582341 A CA2582341 A CA 2582341A CA 2582341 A1 CA2582341 A1 CA 2582341A1
- Authority
- CA
- Canada
- Prior art keywords
- epoxy resin
- composition
- block
- block copolymer
- block segment
- 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
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 140
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 123
- 239000000843 powder Substances 0.000 title claims abstract description 42
- 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 title claims description 18
- 238000000576 coating method Methods 0.000 title abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 96
- 229920001400 block copolymer Polymers 0.000 claims abstract description 85
- 229920000570 polyether Polymers 0.000 claims abstract description 70
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 69
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 30
- 229920000469 amphiphilic block copolymer Polymers 0.000 claims abstract description 29
- 239000008199 coating composition Substances 0.000 claims abstract description 24
- 239000000178 monomer Substances 0.000 claims abstract description 20
- 239000011342 resin composition Substances 0.000 claims abstract description 17
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- -1 nitrogen-containing compound Chemical class 0.000 claims description 44
- 229920005989 resin Polymers 0.000 claims description 42
- 239000011347 resin Substances 0.000 claims description 42
- 239000004593 Epoxy Substances 0.000 claims description 41
- 239000007787 solid Substances 0.000 claims description 21
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 19
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 229920001519 homopolymer Polymers 0.000 claims description 8
- 229920003986 novolac Polymers 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000002460 imidazoles Chemical class 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
- 229920001748 polybutylene Polymers 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- SQZCAOHYQSOZCE-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N=C(N)N=C(N)N SQZCAOHYQSOZCE-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 239000003607 modifier Substances 0.000 claims description 4
- 229920001568 phenolic resin Polymers 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 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
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 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 claims description 2
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical group O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 229920000178 Acrylic resin Polymers 0.000 claims description 2
- 239000004925 Acrylic resin Substances 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 239000002879 Lewis base Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- ZHNUHDYFZUAESO-OUBTZVSYSA-N aminoformaldehyde Chemical compound N[13CH]=O ZHNUHDYFZUAESO-OUBTZVSYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 229930003836 cresol Natural products 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 150000002148 esters Chemical class 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
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 150000007527 lewis bases 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
- 229920001225 polyester resin Polymers 0.000 claims description 2
- 239000004645 polyester resin Substances 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 229920006305 unsaturated polyester Polymers 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- DLMVDBDHOIWEJZ-UHFFFAOYSA-N isocyanatooxyimino(oxo)methane Chemical compound O=C=NON=C=O DLMVDBDHOIWEJZ-UHFFFAOYSA-N 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 239000011248 coating agent Substances 0.000 abstract description 20
- 229920000359 diblock copolymer Polymers 0.000 abstract description 20
- 229920000428 triblock copolymer Polymers 0.000 abstract description 10
- 229920001577 copolymer Polymers 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- 229920001187 thermosetting polymer Polymers 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 12
- 239000012745 toughening agent Substances 0.000 description 12
- 229940106691 bisphenol a Drugs 0.000 description 9
- 239000000693 micelle Substances 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001338 self-assembly Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000004094 surface-active 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
- 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
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000006145 Eagle's minimal essential medium Substances 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001721 carbon Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000013020 final formulation Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000004927 fusion Effects 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
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012768 molten material 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
- 239000002245 particle Substances 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 239000010456 wollastonite Substances 0.000 description 2
- 229910052882 wollastonite Inorganic materials 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
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-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
- 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
- 229920013685 Estron Polymers 0.000 description 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-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
- 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
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910001361 White metal Inorganic materials 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004873 anchoring Methods 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005422 blasting Methods 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
- 239000006229 carbon black Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000010960 cold rolled steel Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004132 cross linking Methods 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
- 230000032798 delamination Effects 0.000 description 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 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
- 238000007590 electrostatic spraying Methods 0.000 description 1
- 229960003399 estrone Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 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
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 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
- 150000002739 metals Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000004482 other powder Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- BPILDHPJSYVNAF-UHFFFAOYSA-M sodium;diiodomethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(I)I BPILDHPJSYVNAF-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000010969 white metal 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/934—Powdered coating composition
-
- 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62661204P | 2004-11-10 | 2004-11-10 | |
| US60/626,612 | 2004-11-10 | ||
| PCT/US2005/039966 WO2006052730A1 (en) | 2004-11-10 | 2005-11-02 | Amphiphilic block copolymer-toughened epoxy resins and powder coatings made therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2582341A1 true CA2582341A1 (en) | 2006-05-18 |
Family
ID=35766914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2582341 Abandoned CA2582341A1 (en) | 2004-11-10 | 2005-11-02 | Amphiphilic block copolymer-toughened epoxy resins and powder coatings made therefrom |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8021586B2 (enExample) |
| EP (1) | EP1812513B1 (enExample) |
| JP (1) | JP5260055B2 (enExample) |
| KR (1) | KR101226377B1 (enExample) |
| CN (1) | CN101056936B (enExample) |
| AT (1) | ATE458788T1 (enExample) |
| BR (1) | BRPI0516703A (enExample) |
| CA (1) | CA2582341A1 (enExample) |
| DE (1) | DE602005019608D1 (enExample) |
| ES (1) | ES2338680T3 (enExample) |
| MX (1) | MX2007005601A (enExample) |
| NO (1) | NO20071761L (enExample) |
| RU (1) | RU2389743C2 (enExample) |
| TW (1) | TW200624520A (enExample) |
| WO (1) | WO2006052730A1 (enExample) |
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| KR20150063590A (ko) | 2007-08-02 | 2015-06-09 | 다우 글로벌 테크놀로지스 엘엘씨 | 열경화성 중합체의 성능을 개선시키기 위한 양친매성 블록 공중합체 및 무기 나노충진제 |
| US8492482B2 (en) * | 2007-12-10 | 2013-07-23 | Arkema Inc. | Acrylic-based rubber modified thermoset composition |
| EP2110397A1 (de) | 2008-04-16 | 2009-10-21 | Sika Technology AG | Auf amphiphilen Block-Copolymer basierendes Polyurethan-Polymer und dessen Verwendung als Schlagzähigkeitsmodifikator |
| EP2128182A1 (de) | 2008-05-28 | 2009-12-02 | Sika Technology AG | Hitzehärtende Epoxidharzzusammensetzung enthaltend einen Beschleuniger mit Heteroatomen |
| EP2145908B1 (de) | 2008-07-17 | 2010-03-24 | 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 |
| EP2182025B1 (de) | 2008-10-31 | 2010-10-06 | Sika Technology AG | Hitzehärtende Epoxidharzzusammensetzungen einsetzbar als Rohbauklebstoff oder Strukturschaum |
| TW201031737A (en) * | 2009-02-03 | 2010-09-01 | Henkel Corp | Encapsulant for inkjet print head |
| US20120010329A1 (en) | 2009-02-24 | 2012-01-12 | Hunter Gary A | Curable epoxy resin compositions and cured products therefrom |
| US20140364540A1 (en) | 2009-02-26 | 2014-12-11 | Jotun Powder Coatings (N) As | Powder coating |
| JP5872903B2 (ja) | 2009-03-09 | 2016-03-01 | ダウ グローバル テクノロジーズ エルエルシー | 両親媒性ブロックコポリマー及びポリオールの組合せを含む熱硬化性組成物並びにそれからの熱硬化生成物 |
| EP2365011A1 (de) | 2010-03-02 | 2011-09-14 | Sika Technology AG | Aminogruppen - terminierter Schlagzähigkeitsmodifikator und dessen Verwendungen in Epoxidharzzusammensetzungen |
| EP2365046A1 (de) | 2010-03-02 | 2011-09-14 | Sika Technology AG | Schlagzäher bei Raumtemperatur härtender zwei-komponentiger Strukturklebstoff |
| WO2012161758A2 (en) * | 2011-02-07 | 2012-11-29 | Valspar Sourcing, Inc. | Coating compositions for containers and other articles and methods of coating |
| EP2794757B1 (en) | 2011-12-20 | 2019-05-15 | Dow Global Technologies LLC | Process for preparing cured epoxy composites |
| KR102173954B1 (ko) * | 2012-08-13 | 2020-11-04 | 헨켈 아이피 앤드 홀딩 게엠베하 | 액체 압축 성형 캡슐화제 |
| US9988508B2 (en) | 2012-08-20 | 2018-06-05 | Mitsubishi Chemical Corporation | Epoxy-resin composition and film, prepreg, and fiber-reinforced plastic using same |
| US9701851B2 (en) * | 2012-10-17 | 2017-07-11 | Dow Global Technologies Llc | Core shell rubber modified solid epoxy resins |
| BR112015010248A2 (pt) * | 2012-11-07 | 2017-07-11 | Dow Global Technologies Llc | composição de resina epóxi curável, processo para preparar a composição de resina epóxi curável e compósito |
| JP6377074B2 (ja) * | 2012-12-20 | 2018-08-22 | ダウ グローバル テクノロジーズ エルエルシー | 無線通信塔のためのポリマー複合体構成部品 |
| CN103387663B (zh) * | 2013-07-29 | 2016-02-17 | 山东理工大学 | 制备端基含巯基的两亲性嵌段共聚物的方法 |
| KR101355979B1 (ko) * | 2013-11-06 | 2014-02-03 | 주식회사 신아티앤씨 | 전기적 특성이 우수한 폴리 에폭시 수지, 이의 조성물 및 제조방법 |
| CN105315614B (zh) * | 2014-07-31 | 2018-10-30 | 太阳油墨（苏州）有限公司 | 印刷电路板的填孔用热固化性树脂组合物、固化物、及印刷电路板 |
| CN107075230A (zh) * | 2014-09-11 | 2017-08-18 | 蓝立方知识产权有限责任公司 | 酯树脂 |
| CN105598858B (zh) * | 2014-10-29 | 2018-11-09 | 厦门精铎建筑科技有限公司 | 热固性树脂结合剂金刚石磨具 |
| WO2016108958A1 (en) | 2014-12-31 | 2016-07-07 | Dow Global Technologies Llc | Crash durable epoxy adhesive compositions having improved low-temperature impact resistance and wash off resistance |
| WO2016197305A1 (en) * | 2015-06-08 | 2016-12-15 | Blue Cube Ip Llc | Coating composition |
| CN106336859B (zh) | 2015-07-07 | 2019-05-24 | 中国石油化工股份有限公司 | 一种组合物及其应用和油基钻井液及提高油基钻井液切力的方法 |
| CN105906814A (zh) * | 2016-06-13 | 2016-08-31 | 四川大学 | 端环氧基聚醚及其制备方法与作为环氧树脂增韧剂的应用 |
| US20200190376A1 (en) | 2016-10-28 | 2020-06-18 | Dow Global Technologies Llc | Crash durable epoxy adhesive having improved low-temperature impact resistance |
| JP7227915B2 (ja) * | 2017-11-02 | 2023-02-22 | 日鉄ケミカル＆マテリアル株式会社 | エポキシ樹脂組成物及びその硬化物 |
| US11820915B2 (en) * | 2018-12-14 | 2023-11-21 | Swimc Llc | Fusion bonded epoxy rebar powder coatings |
| CN110066494B (zh) * | 2019-05-07 | 2022-05-17 | 金安国纪科技（杭州）有限公司 | 环氧树脂组合物及其制备方法和应用、铝基覆铜板 |
| US11459482B2 (en) * | 2020-06-19 | 2022-10-04 | Pall Corporation | Icephobic coating and coated articles |
| JP7541419B2 (ja) * | 2022-04-22 | 2024-08-28 | エル・コーポレイション | アクリレート官能基を有する線状ブロック共重合体強化剤 |
| CN115386282B (zh) * | 2022-10-07 | 2023-04-28 | 浙江绿环新材料科技有限公司 | 一种高效防腐粉末涂料及其制备方法 |
| CN115746261A (zh) * | 2022-12-20 | 2023-03-07 | 江西科技师范大学 | 一种改性环氧聚合物及其制备方法和一种粉末涂料 |
| CN118599399B (zh) * | 2024-06-24 | 2024-11-12 | 浙江捷宇新材料科技股份有限公司 | 一种消防管道用防腐粉末涂料及其制备方法 |
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| 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 |
| JPS5628253A (en) * | 1979-08-17 | 1981-03-19 | Mitsubishi Electric Corp | Epoxy resin composition for powder coating |
| US4431782A (en) | 1981-07-27 | 1984-02-14 | The Dow Chemical Company | Process for the preparation of radiation-curable, water-thinnable vinyl ester resins |
| EP0384896A1 (de) * | 1989-02-24 | 1990-08-29 | Ciba-Geigy Ag | Zähe Epoxidgiessharze |
| US5600019A (en) | 1993-12-17 | 1997-02-04 | The Dow Chemical Company | Polyisocyanate based polymers perpared from formulations including non-silicone surfactants and method for the preparation thereof |
| US5508349A (en) * | 1994-05-09 | 1996-04-16 | Basf Corporation | Reactive flow agent for powder coatings |
| 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 |
| 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 |
| FR2809741B1 (fr) * | 2000-05-31 | 2002-08-16 | Atofina | Materiaux thermodurs a tenue au choc amelioree |
| US6887574B2 (en) * | 2003-06-06 | 2005-05-03 | Dow Global Technologies Inc. | Curable flame retardant epoxy compositions |
| ES2320906T3 (es) * | 2004-04-02 | 2009-05-29 | Dow Global Technologies Inc. | Resinas termoestables endurecidas con copolimero de bloques anfifilico. |
| US7670649B2 (en) * | 2004-11-10 | 2010-03-02 | Dow Global Technologies, Inc. | Amphiphilic block copolymer-toughened epoxy resins and ambient cure high-solids coatings made therefrom |
| WO2006052729A1 (en) * | 2004-11-10 | 2006-05-18 | Dow Global Technologies Inc. | Amphiphilic block copolymer-toughened epoxy resins |
| BRPI0516702A (pt) * | 2004-11-10 | 2008-09-16 | Dow Global Technologies Inc | composição de verniz de resina epóxi para laminados curável, processo para preparar uma composição de verniz para laminados de resina epóxi curável, processo para preparar um laminado, laminado e pré-impregnado |
-
2005
- 2005-11-02 MX MX2007005601A patent/MX2007005601A/es active IP Right Grant
- 2005-11-02 US US11/663,803 patent/US8021586B2/en not_active Expired - Fee Related
- 2005-11-02 EP EP20050818334 patent/EP1812513B1/en not_active Expired - Lifetime
- 2005-11-02 ES ES05818334T patent/ES2338680T3/es not_active Expired - Lifetime
- 2005-11-02 JP JP2007541255A patent/JP5260055B2/ja not_active Expired - Fee Related
- 2005-11-02 BR BRPI0516703-5A patent/BRPI0516703A/pt not_active IP Right Cessation
- 2005-11-02 RU RU2007121664A patent/RU2389743C2/ru not_active IP Right Cessation
- 2005-11-02 AT AT05818334T patent/ATE458788T1/de not_active IP Right Cessation
- 2005-11-02 KR KR1020077010533A patent/KR101226377B1/ko not_active Expired - Fee Related
- 2005-11-02 CA CA 2582341 patent/CA2582341A1/en not_active Abandoned
- 2005-11-02 DE DE200560019608 patent/DE602005019608D1/de not_active Expired - Lifetime
- 2005-11-02 CN CN2005800385431A patent/CN101056936B/zh not_active Expired - Fee Related
- 2005-11-02 WO PCT/US2005/039966 patent/WO2006052730A1/en not_active Ceased
- 2005-11-09 TW TW094139244A patent/TW200624520A/zh unknown
-
2007
- 2007-04-02 NO NO20071761A patent/NO20071761L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20071761L (no) | 2007-08-08 |
| CN101056936B (zh) | 2012-05-23 |
| WO2006052730A1 (en) | 2006-05-18 |
| US8021586B2 (en) | 2011-09-20 |
| DE602005019608D1 (de) | 2010-04-08 |
| ATE458788T1 (de) | 2010-03-15 |
| RU2007121664A (ru) | 2008-12-20 |
| ES2338680T3 (es) | 2010-05-11 |
| JP2008519889A (ja) | 2008-06-12 |
| CN101056936A (zh) | 2007-10-17 |
| MX2007005601A (es) | 2007-05-23 |
| US20080188626A1 (en) | 2008-08-07 |
| KR20070084115A (ko) | 2007-08-24 |
| JP5260055B2 (ja) | 2013-08-14 |
| RU2389743C2 (ru) | 2010-05-20 |
| KR101226377B1 (ko) | 2013-01-24 |
| TW200624520A (en) | 2006-07-16 |
| BRPI0516703A (pt) | 2008-09-16 |
| EP1812513A1 (en) | 2007-08-01 |
| EP1812513B1 (en) | 2010-02-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20131104 |