WO2012048888A1 - Préparation d'un intermédiaire de polyétherimide et son application sur des substrats métalliques - Google Patents
Préparation d'un intermédiaire de polyétherimide et son application sur des substrats métalliques Download PDFInfo
- Publication number
- WO2012048888A1 WO2012048888A1 PCT/EP2011/005166 EP2011005166W WO2012048888A1 WO 2012048888 A1 WO2012048888 A1 WO 2012048888A1 EP 2011005166 W EP2011005166 W EP 2011005166W WO 2012048888 A1 WO2012048888 A1 WO 2012048888A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyetherimide
- coating
- preparing
- metal substrate
- coated metal
- Prior art date
Links
- 229920001601 polyetherimide Polymers 0.000 title claims abstract description 137
- 239000004697 Polyetherimide Substances 0.000 title claims abstract description 129
- 239000000758 substrate Substances 0.000 title claims abstract description 77
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 35
- 239000002184 metal Substances 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title description 3
- 238000000576 coating method Methods 0.000 claims abstract description 71
- 239000011248 coating agent Substances 0.000 claims abstract description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000002244 precipitate Substances 0.000 claims abstract description 20
- 239000003960 organic solvent Substances 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 13
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 230000001376 precipitating effect Effects 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 3
- 238000001914 filtration Methods 0.000 claims abstract description 3
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 238000005260 corrosion Methods 0.000 claims description 26
- 230000007797 corrosion Effects 0.000 claims description 25
- 229910000831 Steel Inorganic materials 0.000 claims description 19
- 239000010959 steel Substances 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 12
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 12
- 150000004985 diamines Chemical class 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 150000007530 organic bases Chemical class 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000004411 aluminium Substances 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- 229910000077 silane Inorganic materials 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000004984 aromatic diamines Chemical class 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 239000002105 nanoparticle Substances 0.000 claims description 3
- HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052621 halloysite Inorganic materials 0.000 claims description 2
- 238000013086 organic photovoltaic Methods 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 37
- 239000000543 intermediate Substances 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- -1 aromatic anhydride Chemical class 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000008901 benefit Effects 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- 230000006872 improvement Effects 0.000 description 6
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 5
- 229940018564 m-phenylenediamine Drugs 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 150000004756 silanes Chemical class 0.000 description 4
- FIXBBOOKVFTUMJ-UHFFFAOYSA-N 1-(2-aminopropoxy)propan-2-amine Chemical compound CC(N)COCC(C)N FIXBBOOKVFTUMJ-UHFFFAOYSA-N 0.000 description 3
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 3
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical group C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002390 adhesive tape Substances 0.000 description 3
- 229910021387 carbon allotrope Inorganic materials 0.000 description 3
- 229910021393 carbon nanotube Inorganic materials 0.000 description 3
- 239000002041 carbon nanotube Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 125000001033 ether group Chemical group 0.000 description 3
- IWBOPFCKHIJFMS-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl) ether Chemical compound NCCOCCOCCN IWBOPFCKHIJFMS-UHFFFAOYSA-N 0.000 description 3
- 238000010907 mechanical stirring Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 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
- 229910001297 Zn alloy Inorganic materials 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- 150000002169 ethanolamines Chemical class 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229920005575 poly(amic acid) Polymers 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 1
- PCAXITAPTVOLGL-UHFFFAOYSA-N 2,3-diaminophenol Chemical compound NC1=CC=CC(O)=C1N PCAXITAPTVOLGL-UHFFFAOYSA-N 0.000 description 1
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
- BPGIOCZAQDIBPI-UHFFFAOYSA-N 2-ethoxyethanamine Chemical compound CCOCCN BPGIOCZAQDIBPI-UHFFFAOYSA-N 0.000 description 1
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 1
- WFNVGXBEWXBZPL-UHFFFAOYSA-N 3,5-diaminophenol Chemical compound NC1=CC(N)=CC(O)=C1 WFNVGXBEWXBZPL-UHFFFAOYSA-N 0.000 description 1
- JCEZOHLWDIONSP-UHFFFAOYSA-N 3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propan-1-amine Chemical compound NCCCOCCOCCOCCCN JCEZOHLWDIONSP-UHFFFAOYSA-N 0.000 description 1
- JBOYAGICRPDZIA-UHFFFAOYSA-N 3h-1,3-benzothiazole-2-thione;1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(=S)NC2=C1.C1=CC=C2SC(=S)NC2=C1 JBOYAGICRPDZIA-UHFFFAOYSA-N 0.000 description 1
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 239000002211 L-ascorbic acid Substances 0.000 description 1
- 235000000069 L-ascorbic acid Nutrition 0.000 description 1
- 101100098799 Magnaporthe oryzae (strain 70-15 / ATCC MYA-4617 / FGSC 8958) TAS2 gene Proteins 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 101150002629 TAS1 gene Proteins 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- WAKZZMMCDILMEF-UHFFFAOYSA-H barium(2+);diphosphate Chemical compound [Ba+2].[Ba+2].[Ba+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O WAKZZMMCDILMEF-UHFFFAOYSA-H 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 239000010960 cold rolled steel Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 239000000176 sodium gluconate Substances 0.000 description 1
- 229940005574 sodium gluconate Drugs 0.000 description 1
- 235000012207 sodium gluconate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
- C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
- C08G73/1082—Partially aromatic polyimides wholly aromatic in the tetracarboxylic moiety
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/0248—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies
- H01L31/036—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies characterised by their crystalline structure or particular orientation of the crystalline planes
- H01L31/0392—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies characterised by their crystalline structure or particular orientation of the crystalline planes including thin films deposited on metallic or insulating substrates ; characterised by specific substrate materials or substrate features or by the presence of intermediate layers, e.g. barrier layers, on the substrate
- H01L31/03926—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies characterised by their crystalline structure or particular orientation of the crystalline planes including thin films deposited on metallic or insulating substrates ; characterised by specific substrate materials or substrate features or by the presence of intermediate layers, e.g. barrier layers, on the substrate comprising a flexible substrate
- H01L31/03928—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by their semiconductor bodies characterised by their crystalline structure or particular orientation of the crystalline planes including thin films deposited on metallic or insulating substrates ; characterised by specific substrate materials or substrate features or by the presence of intermediate layers, e.g. barrier layers, on the substrate comprising a flexible substrate including AIBIIICVI compound, e.g. CIS, CIGS deposited on metal or polymer foils
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/541—CuInSe2 material PV cells
Definitions
- the present invention relates to a method of preparing a polyetherimide coated metal substrate, a precipitate of a polyetherimide intermediate, the coated metal substrate itself and to the use of the polyetherimide coated substrate in a photovoltaic device.
- Polyetherimides are typically prepared by reacting an aromatic anhydride of a tetracarboxylic acid with an aromatic diamine in an organic solvent. The resulting polyamic acid solution is then heated to convert the polyamic acid into the corresponding polyetherimide. Polyetherimides obtained in this way generally exhibit excellent, mechanical strength, electrical properties, solvent resistance and heat resistance, i.e. they do not show signs of degradation or deformation at elevated temperatures. The use of aromatic polyetherimides has been limited principally to the electronic and medical industries.
- a characteristic of aromatic polyetherimide synthesis is the use of large quantities of organic solvents and due to the limited solubility of the aromatic starting materials, most reactions are carried out in the presence of organic solvents such as N-methyl pyrrolidone, N,N- dimethylacetamide or Dimethylformamide, these are known to be hazardous and toxic.
- organic solvents such as N-methyl pyrrolidone, N,N- dimethylacetamide or Dimethylformamide, these are known to be hazardous and toxic.
- the polyetherimides thus produced are typically semi-crystalline, rigid and poor in formability.
- a further object of the present invention is to a provide a polyetherimide coated substrate wherein the coating has improved flexibility and corrosion resistance.
- a method of preparing a polyetherimide coated metal substrate which comprises the steps of applying a water based solution comprising a polyetherimide intermediate on a substrate to form a coating and subjecting the coated substrate to a heat treatment such that the coating is dried and cured.
- the water based solution is prepared by mixing an aromatic dianhydride or derivative thereof and a first aliphatic polyetherdiamine in an organic solvent solution; subjecting this solution to a heat treatment to form a polyetherimide intermediate; precipitating the polyetherimide intermediate from the organic solvent; filtering and drying the precipitate and providing the dried precipitate in a water based solution.
- polyetherimide intermediates of the present invention are water-soluble. This means that organic solvents are only required in the preparation of the polyetherimide intermediate and not when applying the polyetherimide intermediate on the metal substrate. This offers the manufacturer a significant advantage since the application of a water-based solution avoids the environmental and handling issues associated with organic solvents.
- a further advantage of the present invention is that after the step of precipitating the polyetherimide intermediate from the organic solvent, the organic solvent can be recovered and re-used in the synthesis of more polyetherimides; this offers the manufacturer a significant cost advantage.
- the polyetherimide intermediate is precipitated from an organic solvent into an aprotic neutral solvent such as acetone or an acetone/methanol mixture and then dissolved in water.
- polyetherimide intermediates having a molecular weight up to 100000 can be obtained. Consequently, the final polyetherimide coating will possess improved corrosion resistance and formability.
- polyetherimide intermediates can be prepared in water, the maximum molecular weight obtainable is below 10000 and therefore the corresponding polyetherimide coatings tend to exhibit reduced formability and corrosion resistance by comparison.
- the first polyetherdiamine contains at least one primary amino group attached to the terminus of a polyether backbone, wherein the polyether backbone is based either on propylene oxide (PO), ethylene oxide (EO), or mixed EO/PO.
- PO propylene oxide
- EO ethylene oxide
- mixed EO/PO mixed EO/PO
- Particularly suitable first polyetherdiamines include 0,0'-Bis(2-aminopropyl) polypropylene glycol-Woc/ -polyethylene glycol-Woc/ -polypropylene glycol (J1), 4,7,10- trioxa-1 ,13- tridecanediamine (J2), Poly(propylene glycol) bis(2-aminopropyl ether having a molecular weight 230 (J3), Poly(propylene glycol) bis(2-aminopropyl ether having a molecular weight of 400 (J4) and 1 ,2-bis(2-aminoethoxyethane) (J5).
- a further advantage is that coatings comprising any one of the above first polyetherdiamines exhibit improved flexibility relative to aromatic polyetherdimides.
- a third advantage is that by using first diamines as above, the glass transition temperature of the polyetherimide intermediate is significantly reduced which enables lower temperatures to be used during the curing. A significant improvement in polyetherimide processing is therefore achieved.
- the polyetherimide intermediate comprises an aromatic polyetherdiamine and/or a monoaromatic diamine.
- the aromatic polyetherdiamine and/or monoaromatic diamine is mixed together with the aromatic dianhydride or derivative thereof and the first aliphatic polyetherdiamine in the organic solvent solution.
- the aromatic groups of the polyetherdiamine contribute to improving the overall corrosion resistance and mechanical strength of the polyetherimide coating, whereas the ether groups improve the adhesion of the coating to the metal substrate.
- the aromatic polyetherdiamine is 4,4'-(1 ,3-Phenylenedioxy)dianiline (M1 ).
- a monoaromatic diamine and preferably a meta substituted monoaromatic diamine in the polyetherimide intermediate is advantageous since meta substituted diamines disrupt intermolecular interactions that lead to mesophase behaviour and a reduction in the formability of polyetherimide coatings.
- Preferred monoaromatic diamines include m- phenylenediamine (MPA).
- MPA m- phenylenediamine
- Other aromatic diamines that can be used alone or in combination with MPA include diaminobenzoic acid (DABA), 2,6-diaminopyridine (DAPY) or 3,5- diaminophenol (DAPH).
- DABA diaminobenzoic acid
- DAPY 2,6-diaminopyridine
- DAPH 3,5- diaminophenol
- the aforementioned diamines provide carboxylic acid, pyridine and hydroxyl functional groups respectively, which can interact with the metal substrate through acid-base interactions and/or H-bonding.
- the polyetherimide is reacted with an organic base to form a water-soluble salt of the polyetherimide intermediate.
- the organic base is a high boiling point amine having a boiling point of at least 150 ° C.
- Organic bases used in accordance with the invention are, but not limited to N-butyldiethanol amine, 2-aminoethanol , 2-dimethylamino ethanol, N,N- diethylethanol amines, ⁇ , ⁇ -dimethylethanol and 2-amino-2methyl-1-propanol.
- Alkylamines such as triethylamine, tripropylamine, tributylamine have also been used.
- the high boiling point amine has a boiling point of at least 150 ° C at atmospheric pressure.
- the polyetherimide coating comprises the organic base after the step of subjecting the polyetherimide intermediate coated substrate to the heat treatment.
- ethanolamines such as N-butyldiethanol amine (BP: 262 ° C) are not removed from the applied coating because their boiling points are greater than the temperatures used in the curing cycle.
- BP N-butyldiethanol amine
- the use of such ethanolamines results in polyetherimide coatings having excellent flexibility, adhesion and corrosion resistance. This unexpected improvement in physical and anti-corrosion properties is attributed in part to the presence of the ethanolamine in the cured polyetherimide coating.
- the precipitate is reacted with a second aliphatic polyetherdiamine, preferably a polyetherdiamine containing at least one primary amino group attached to the terminus of a polyether backbone, wherein the polyether backbone is based either on propylene oxide (PO), ethylene oxide (EO), or mixed EO/PO.
- a second aliphatic polyetherdiamine preferably a polyetherdiamine containing at least one primary amino group attached to the terminus of a polyether backbone, wherein the polyether backbone is based either on propylene oxide (PO), ethylene oxide (EO), or mixed EO/PO.
- PO propylene oxide
- EO ethylene oxide
- mixed EO/PO mixed EO/PO
- the first and/or second polyetherdiamine contains between 2 and 20 ether linkages, preferably between 2 and 13 ether linkages and more preferably between 2 and 6 ether linkages.
- the use of aliphatic polyetherdiamines having a higher number of ether groups improves the formability and adhesion of the polyetherimide coating. If more than 20 ether linkages are present along the backbone of polyetherimide then coating performance deteriorates. Aliphatic polyetherdiamines that possess a lower number of ether groups exhibit a reduction in polyetherimide coating flexibility but an increase in the corrosion resistance of the polyetherimide coating.
- the polyetherimide intermediate comprises an epoxy based silane.
- Polyetherimides comprising epoxy based silanes exhibit improvements in coating adhesion relative to polyetherimides where epoxy based silanes are absent.
- polyetherimides comprising epoxy based silanes exhibit less than 10% delamination from the metal substrate when assessed using a scratch tape test (ASTM D 3359).
- the metal substrate is a steel strip, sheet, wire, rebar or blank.
- the steel is a carbon steel, a cold-rolled steel or a hot-rolled steel.
- the polyetherimide coating is able to interact strongly with the underlying steel substrate through acid-base interactions and/or hydrogen bonding, leading to an improvement in coating adhesion.
- Other metal substrates on which the polyetherimide coating may be provided include aluminium, copper, nickel, tin, zinc or brass. Providing a coated metal substrate having improved corrosion and adhesion properties is of particular importance to the automotive industry and white good industries where the coated metal substrate should exhibit very high corrosion resistance to extend the lifetime of coated substrate.
- the metal substrate comprises a coating selected from the group consisting of aluminium, zinc, zinc oxide, zinc and aluminium, nickel, magnesium, silane or zirconium.
- metal substrates comprising aluminium, zinc alloys of aluminium and zinc, magnesium and/or nickel provide galvanic corrosion protection, if for instance, the metal substrate is a steel substrate.
- Metal substrates comprising coatings of silanes and/or zirconium offer improved adhesion properties due to the presence of covalent bonds between the silane and/or zirconium and the metal substrate.
- the polyetherimide coating comprises a metal oxide nanoparticle, a corrosion inhibitor or a halloysite or a mixture thereof.
- Preferred metal oxide nano-particles include silica, titania, magnesia, alumina or carbon nanotubes. The particles are used to improve the corrosion resistance of the polyetherimide coating.
- Preferred corrosion inhibitors include sodium gluconate, sodium benzoate, L-Ascorbic acid, 8-hydroxy quinine, n- benzotrizole, mercaptobenzimidazol mercaptobenzothiazole or derivatives thereof.
- Preferred halloysites that are used for the controlled release of corrosion inhibitors include calcium carbonate, zeolites, barium sulphate, barium phosphate, copper ferrocyanites, carbon nanotubes and kalonites.
- the water based solution comprising the polyetherimide intermediate can also be provided with coating additives (defoamers, levelling agents and viscosity modifiers) to improve the processability of the water based solution before its application on the steel substrate.
- coating additives defoamers, levelling agents and viscosity modifiers
- Dyes can be used to tailor the aesthetic properties of the polyetherimide coating.
- the water based solution comprises an allotrope of carbon, preferably graphene, carbon nanotubes or carbon black.
- the presence of the allotrope of carbon in the resulting polyetherimide coating increases the conductivity of the coating to an extent that the polyetherimide coated substrate is more suitable for use in the automotive industry where the welding of such coated metal substrates is of importance.
- the water based solution may comprise a carbon allotrope content of up to 30 wt% without adversely affecting the processability of the water based solution or the uniformity of the polyetherimide coating after curing. A carbon allotrope content above 30 wt% results in the polyetherimide coating having reduced corrosion resistance and as a consequence the longevity of the polyetherimide coated substrate will also be reduced.
- Water based solutions comprising 0.1 -5 wt%, preferably 0.5-2 wt% of the carbon allotrope are preferred since they result in polyetherimide coatings having improved conductivity, corrosion resistance, flexibility and adhesion.
- a polyetherimide coated substrate which polyetherimide coating comprises an aromatic dianhydride or derivative thereof and an aromatic diamine, said polyetherimide coating having a dry film thickness of 1- 10 ⁇ , preferably 1-5 im and more 1-3 ⁇ .
- both thick ( ⁇ 10 ⁇ ) and thin polyetherimide coatings ( ⁇ 5 ⁇ ) exhibit an improvement in corrosion resistance whereas thin coatings also improve coating performance with respect to weldability and formability.
- the polyetherimide of the polyetherimide coated metal substrate has a coating thickness of 10 pm or below since with higher thicknesses the polyetherimide may delaminate from the metal substrate.
- the polyetherimide coating of the polyetherimide coated substrate is used as an electrically insulating layer in a photovoltaic device, preferably an organic photovoltaic device and more preferably in a dye sensitised solar cell.
- a photovoltaic device preferably an organic photovoltaic device and more preferably in a dye sensitised solar cell.
- the dye sensitised solar cell has a reverse design.
- the polyetherimide coating of the present invention has a temperature resistance between 400 and 500°C. By temperature resistance it is meant that the polyetherimide coating does not thermally degrade within the temperature range specified. Such temperatures are typically used when sintering the semi-conductive layer of the dye sensitised solar cell.
- the polyetherimide coating is also resistant to the electrolyte of the dye-sensitised solar cell, preventing the underlying metal substrate from being corroded, thereby extending the lifetime of the cell.
- a polyetherimide intermediate precipitate which polyetherimide comprises an aromatic dianhydride or derivative thereof and a first aliphatic polyetherdiamine.
- the polyetherimide precipitate is produced according to the method of the first aspect of the invention.
- the embodiments and the advantages relating to the first aspect of the invention similarly apply to the fourth aspect of the invention.
- a 200mL one neck vessel equipped with a nitrogen inlet is charged with 2,2' - (Ethylenedioxy)bis(ethylamine) J5 (14mmol, 4.24g), 3,5-diaminobenzoic acid (2mmol, 0.31 g) (DABA) and NMP (40g).
- This solution is stirred at 80°C for 5 minutes before 4,4-Biphthalic anhydride (14mmol, 4.24) is added to the stirred solution.
- This stirred solution is stirred for a further 12hrs at 80°C.
- a 100 mL one necked vessel equipped with a nitrogen inlet is charged with 1 ,3-bis(4- aminophenoxy)benzene M1 (3.5 mmol, 1.04 g), m-phenylenediamine (1.5 mmol, 0.16 g) and N P (23g).
- 4,4-Biphthalic anhydride (5 mmol, 1.51 g) is then added and this solution is stirred under inert conditions for 8hrs to form a polyetherimide intermediate.
- Triethylamine (10 mmol, 1.01 g) is added to this stirred solution and the solution is stirred for an additional hour. It is then transferred into acetone or an acetone/methanol mixture under mechanical stirring, which causes the polyetherimide intermediate to precipitate.
- the precipitate is dried at 50°C.
- a 10 % wt solution of the dried precipitate is prepared in water; 1 wt % of triethylamine is added to ease the dissolution.
- This solution is applied on a steel substrate dried at a temperature of 80°C for 5 minutes and cured between 200 and 250°C for 5 minutes to form the corresponding polyetherimide.
- a 100 mL one necked vessel equipped with a nitrogen inlet is charged with 2,2' - (Ethylenedioxy)bis(ethylamine) J5 (3.5 mmol, 0.5187 g), m-phenylelenediamine (1.5 mmol, 0.16 g) and NMP (23g).
- 4,4-Biphthalic anhydride (5 mmol, 1.51 g) is added and this solution is stirred under inert conditions for 8hrs to form a polyetherimide intermediate.
- N-butyldiethanol amine (5 mmol, 0.8g) is added to this stirred solution, which is stirred for an additional hour.
- a 100 mL one necked vessel equipped with a nitrogen inlet is charged with 2,2' - (Ethylenedioxy)bis(ethylamine) J5 (3.5 mmol, 0.5187 g), m-phenylelenediamine (1.5 mmol, 0.16 g) and NMP (23g).
- 4,4-Biphthalic anhydride (5 mmol, 1.51 g) is added and this solution is stirred under inert conditions for 8hrs to form a polyetherimide intermediate.
- Tripropylamine (5 mmol, 0.7 g) is added to this stirred solution, which is stirred for an additional hour.
- This stirred solution is then transferred into acetone or an acetone/methanol mixture under mechanical stirring causing the polyetherimide intermediate to precipitate.
- the precipitate is dried at 50°C.
- a 10 % wt solution of the dried precipitate is prepared in water;if necessary 1 wt % of tripropylamine amine is added to ease the dissolution.
- This solution is applied on a steel substrate, dried at a temperature of 80 ° C for 5 minutes and cured between 200 * C and 250 "C for 5 minutes to form the corresponding polyetherimide.
- Comparative example C1 relates to a polyetherimide coated steel substrate wherein the polyetherimide consists of BPDA and 4,4'-(1 ,3-Phenylenedioxy)dianiline (M1).
- the polyetherimide of C1 was prepared in 100% organic solvent.
- Example 2 is a comparative example (C2), which relates to a polyetherimide coated substrate wherein the polyetherimide consists of BPDA, M1 and MPA. This polyetherimide was prepared in organic solvent and applied on the substrate in a water based solution.
- the polyetherimide coated substrates were then subjected to a number of tests to assess the corrosion resistance, flexibility and adhesion of the polyetherimide coatings.
- the results of the aforementioned tests can be seen in Tablel .
- the thermal stability of the polyetherimide coatings was assessed by thermo-gravimetric analysis using a Perkin Elmer pyris diamond DMA. Polyetherimide coatings were heated at a rate of 10°C/min over a temperature range of 25°C to 600°C. Using the same apparatus it was also possible to determine the temperature for 10% weight loss which is a measure of polymer stability.
- the Salt spray test (ASTM B117 standard) is used to measure the corrosion resistance of coated and uncoated metallic specimens, when exposed to a salt spray at elevated temperature.
- Polyetherimide coated steel substrates were placed in an enclosed chamber at 35 °C and exposed to a continuous indirect spray (fogging) of 5% salt solution (pH 6.5 to 7.2), which falls-out on to the coated steel substrate at a rate of 1.0 to 2.0 ml/80cm 2 /hour.
- the fogging of 5% salt solution is at the specified rate and the fog collection rate is determined by placing a minimum of two 80 sq. cm. funnels inserted into measuring cylinders graduated in ml. inside the chamber. This climate is maintained under constant steady state conditions. The samples are placed at a 15-30 degree angle from vertical.
- the test duration is variable.
- the sample size is 76 x 127 x 0.8 mm, are cleaned, weighed, and placed in the chamber in the proximity of the collector funnels. After exposure the panels are critically observed for blisters, red rust spots and delaminations.
- Polyetherimide coated steel substrates were deemed to have excellent corrosion resistance if 10% or less of the substrate surface was covered by red rust and/or blisters.
- Polyetherimide coated steel substrates were deemed to have good corrosion resistance if 11 -15% of the substrate surface was covered by red rust and/or blisters.
- Polyetherimide coated steel substrates were deemed to have bad corrosion resistance if greater than 15% of the substrate surface is covered by red rust and/or blisters.
- Coating flexibility was analysed using an Erichsen cupping test (ISO 20482), which is a ductility test that is typically employed to evaluate the ability of metallic sheets and strips to undergo plastic deformation in stretch forming. Cups were made using 5KN pressure. If no cracks are observed during the Erichsen cupping test then the flexibility of the coating is excellent. If one or more cracks are observed then the flexibility of the coating is bad.
- ISO 20482 Erichsen cupping test
- Adhesion was evaluated by a scratch tape test (ASTM D 3359), which is a method for assessing the adhesion of coating films to metallic substrates by applying and removing pressure sensitive tape over cuts made in the film. If 5% or less of the coating was removed by the adhesive tape then the adhesion of the coating to the steel substrate is excellent. If 6-15 % of the coating was removed by the adhesive tape then coating adhesion is good, and if the adhesive tape removed greater than 15% of the coating then coating adhesion was bad.
- ASTM D 3359 is a method for assessing the adhesion of coating films to metallic substrates by applying and removing pressure sensitive tape over cuts made in the film. If 5% or less of the coating was removed by the adhesive tape then the adhesion of the coating to the steel substrate is excellent. If 6-15 % of the coating was removed by the adhesive tape then coating adhesion is good, and if the adhesive tape removed greater than 15% of the coating then coating adhesion was bad.
- Table 1 Overview of corrosion resistance, flexibility and adhesion properties of polyetherimide coatings on steel substrates, wherein *** is excellent, ** is good, * is bad coating performance.
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Abstract
L'invention porte sur un procédé de préparation d'un substrat métallique revêtu de polyétherimide qui comprend les étapes consistant à appliquer une solution à base d'eau comprenant un intermédiaire de polyétherimide sur un substrat pour former un revêtement et soumettre le substrat enduit à un traitement thermique de façon à sécher et faire durcir le revêtement, la solution à base d'eau étant préparée par mélange d'un dianhydride aromatique ou d'un dérivé de celui-ci et d'une première polyétherdiamine aliphatique dans une solution de solvant organique ; le fait de soumettre cette solution à un traitement thermique pour former un intermédiaire de polyétherimide ; la précipitation de l'intermédiaire de polyétherimide dans le solvant organique ; la filtration et le séchage du précipité et l'utilisation du précipité séché dans une solution à base d'eau.
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JP2015195315A (ja) * | 2014-03-31 | 2015-11-05 | 株式会社神戸製鋼所 | 金属基板 |
CN108503831A (zh) * | 2017-02-24 | 2018-09-07 | 财团法人纺织产业综合研究所 | 用以形成聚酰亚胺的组成物、聚酰亚胺及聚酰亚胺膜 |
CN111777733A (zh) * | 2020-08-07 | 2020-10-16 | 宁波耀众模塑科技有限公司 | 一种聚氨酯发泡产品用阻燃异氰酸根混合物 |
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US20090288699A1 (en) * | 2008-05-20 | 2009-11-26 | E.I. Du Pont De Nemours And Company | Laminate structures for high temperature photovoltaic applications, and methods relating thereto |
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JP2015195315A (ja) * | 2014-03-31 | 2015-11-05 | 株式会社神戸製鋼所 | 金属基板 |
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CN108503831B (zh) * | 2017-02-24 | 2021-02-26 | 财团法人纺织产业综合研究所 | 用以形成聚酰亚胺的组成物、聚酰亚胺及聚酰亚胺膜 |
CN111777733A (zh) * | 2020-08-07 | 2020-10-16 | 宁波耀众模塑科技有限公司 | 一种聚氨酯发泡产品用阻燃异氰酸根混合物 |
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