JP5914907B2 - 防錆剤および表面処理金属材 - Google Patents
防錆剤および表面処理金属材 Download PDFInfo
- Publication number
- JP5914907B2 JP5914907B2 JP2008303887A JP2008303887A JP5914907B2 JP 5914907 B2 JP5914907 B2 JP 5914907B2 JP 2008303887 A JP2008303887 A JP 2008303887A JP 2008303887 A JP2008303887 A JP 2008303887A JP 5914907 B2 JP5914907 B2 JP 5914907B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- acid
- group
- chelate
- stretch
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 title claims description 65
- 229910052751 metal Inorganic materials 0.000 title claims description 47
- 239000002184 metal Substances 0.000 title claims description 47
- 230000003449 preventive effect Effects 0.000 title description 33
- 150000001875 compounds Chemical class 0.000 claims description 84
- 239000013522 chelant Substances 0.000 claims description 46
- 125000001165 hydrophobic group Chemical group 0.000 claims description 28
- 239000007769 metal material Substances 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 21
- 239000003446 ligand Substances 0.000 claims description 14
- 239000003112 inhibitor Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 229910052782 aluminium Inorganic materials 0.000 claims description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 10
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 229910000838 Al alloy Inorganic materials 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910000881 Cu alloy Inorganic materials 0.000 claims description 5
- 229910000640 Fe alloy Inorganic materials 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims description 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- 239000003795 chemical substances by application Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- -1 tetrapyrroles Chemical class 0.000 description 20
- 239000002253 acid Substances 0.000 description 19
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 230000002265 prevention Effects 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- 230000007935 neutral effect Effects 0.000 description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 10
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 241001163841 Albugo ipomoeae-panduratae Species 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 230000008602 contraction Effects 0.000 description 8
- 125000005594 diketone group Chemical group 0.000 description 8
- 150000002085 enols Chemical class 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000002738 chelating agent Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000001993 wax Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- JYXGIOKAKDAARW-UHFFFAOYSA-N N-(2-hydroxyethyl)iminodiacetic acid Chemical compound OCCN(CC(O)=O)CC(O)=O JYXGIOKAKDAARW-UHFFFAOYSA-N 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 229960000735 docosanol Drugs 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- VLLNJDMHDJRNFK-UHFFFAOYSA-N adamantan-1-ol Chemical compound C1C(C2)CC3CC2CC1(O)C3 VLLNJDMHDJRNFK-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 235000012000 cholesterol Nutrition 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 238000001139 pH measurement Methods 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 229920000388 Polyphosphate Polymers 0.000 description 3
- 239000002262 Schiff base Substances 0.000 description 3
- 150000004753 Schiff bases Chemical class 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 150000002678 macrocyclic compounds Chemical class 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- BASNZTUXPUAQLZ-UHFFFAOYSA-N nonadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCC(Cl)=O BASNZTUXPUAQLZ-UHFFFAOYSA-N 0.000 description 3
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000001205 polyphosphate Substances 0.000 description 3
- 235000011176 polyphosphates Nutrition 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- URDCARMUOSMFFI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O URDCARMUOSMFFI-UHFFFAOYSA-N 0.000 description 2
- WYMDDFRYORANCC-UHFFFAOYSA-N 2-[[3-[bis(carboxymethyl)amino]-2-hydroxypropyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)CN(CC(O)=O)CC(O)=O WYMDDFRYORANCC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000021357 Behenic acid Nutrition 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 229940116226 behenic acid Drugs 0.000 description 2
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- FFVHXGZXDRXFLQ-UHFFFAOYSA-N cyclopentadecanol Chemical compound OC1CCCCCCCCCCCCCC1 FFVHXGZXDRXFLQ-UHFFFAOYSA-N 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 2
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- KFEVDPWXEVUUMW-UHFFFAOYSA-N docosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 KFEVDPWXEVUUMW-UHFFFAOYSA-N 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- IFQUWYZCAGRUJN-UHFFFAOYSA-N ethylenediaminediacetic acid Chemical compound OC(=O)CNCCNCC(O)=O IFQUWYZCAGRUJN-UHFFFAOYSA-N 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 2
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- FJRPWCNFWGBGOF-UHFFFAOYSA-N tridecanoyl chloride Chemical compound CCCCCCCCCCCCC(Cl)=O FJRPWCNFWGBGOF-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- BAERPNBPLZWCES-UHFFFAOYSA-N (2-hydroxy-1-phosphonoethyl)phosphonic acid Chemical compound OCC(P(O)(O)=O)P(O)(O)=O BAERPNBPLZWCES-UHFFFAOYSA-N 0.000 description 1
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
- QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-ol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-QCYZZNICSA-N 0.000 description 1
- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 description 1
- UOFGSWVZMUXXIY-UHFFFAOYSA-N 1,5-Diphenyl-3-thiocarbazone Chemical compound C=1C=CC=CC=1N=NC(=S)NNC1=CC=CC=C1 UOFGSWVZMUXXIY-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- XSOHXMFFSKTSIT-UHFFFAOYSA-N 1-adamantylmethanamine Chemical compound C1C(C2)CC3CC2CC1(CN)C3 XSOHXMFFSKTSIT-UHFFFAOYSA-N 0.000 description 1
- PVSNMDAHWMHSBD-UHFFFAOYSA-N 1-cyclohexylcyclohexan-1-ol Chemical compound C1CCCCC1C1(O)CCCCC1 PVSNMDAHWMHSBD-UHFFFAOYSA-N 0.000 description 1
- SNJMEUDNDRSJAS-UHFFFAOYSA-N 2-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(CCN)C3 SNJMEUDNDRSJAS-UHFFFAOYSA-N 0.000 description 1
- KKLMJYDGZSAIQX-UHFFFAOYSA-N 2-(n-hydroxyanilino)acetic acid Chemical compound OC(=O)CN(O)C1=CC=CC=C1 KKLMJYDGZSAIQX-UHFFFAOYSA-N 0.000 description 1
- ZYXNLVMBIHVDRH-UHFFFAOYSA-N 2-Methylpropyl 3-oxobutanoate Chemical compound CC(C)COC(=O)CC(C)=O ZYXNLVMBIHVDRH-UHFFFAOYSA-N 0.000 description 1
- RAZLJUXJEOEYAM-UHFFFAOYSA-N 2-[bis[2-(2,6-dioxomorpholin-4-yl)ethyl]azaniumyl]acetate Chemical compound C1C(=O)OC(=O)CN1CCN(CC(=O)O)CCN1CC(=O)OC(=O)C1 RAZLJUXJEOEYAM-UHFFFAOYSA-N 0.000 description 1
- UBGQOSNFVJFTLZ-UHFFFAOYSA-N 2-[carboxymethyl-[(4-ethenylphenyl)methyl]amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC1=CC=C(C=C)C=C1 UBGQOSNFVJFTLZ-UHFFFAOYSA-N 0.000 description 1
- WWXISJJRNIVDIP-UHFFFAOYSA-N 2-[carboxymethyl-[2-[carboxymethyl(hydroxymethyl)amino]ethyl]amino]acetic acid Chemical compound OC(=O)CN(CO)CCN(CC(O)=O)CC(O)=O WWXISJJRNIVDIP-UHFFFAOYSA-N 0.000 description 1
- UEBUOANSKOYYKC-UHFFFAOYSA-N 2-ethyladamantan-1-ol Chemical compound C1C(C2)CC3CC1C(CC)C2(O)C3 UEBUOANSKOYYKC-UHFFFAOYSA-N 0.000 description 1
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
- OXHVCLNCFNQWON-UHFFFAOYSA-N 2-methyladamantan-1-ol Chemical compound C1C(C2)CC3CC1C(C)C2(O)C3 OXHVCLNCFNQWON-UHFFFAOYSA-N 0.000 description 1
- OFLNEVYCAMVQJS-UHFFFAOYSA-N 2-n,2-n-diethylethane-1,1,1,2-tetramine Chemical compound CCN(CC)CC(N)(N)N OFLNEVYCAMVQJS-UHFFFAOYSA-N 0.000 description 1
- CJAZCKUGLFWINJ-UHFFFAOYSA-N 3,4-dihydroxybenzene-1,2-disulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C(S(O)(=O)=O)=C1O CJAZCKUGLFWINJ-UHFFFAOYSA-N 0.000 description 1
- HTDKBQNYLUMSQH-UHFFFAOYSA-N 3-hydroxypropyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCO HTDKBQNYLUMSQH-UHFFFAOYSA-N 0.000 description 1
- QDPGMJHSCAQOSZ-UHFFFAOYSA-N 3h-dithiole;toluene Chemical compound C1SSC=C1.CC1=CC=CC=C1 QDPGMJHSCAQOSZ-UHFFFAOYSA-N 0.000 description 1
- POLIXZIAIMAECK-UHFFFAOYSA-N 4-[2-(2,6-dioxomorpholin-4-yl)ethyl]morpholine-2,6-dione Chemical compound C1C(=O)OC(=O)CN1CCN1CC(=O)OC(=O)C1 POLIXZIAIMAECK-UHFFFAOYSA-N 0.000 description 1
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 239000004380 Cholic acid Substances 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 1
- DTGKSKDOIYIVQL-MRTMQBJTSA-N Isoborneol Natural products C1C[C@@]2(C)[C@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-MRTMQBJTSA-N 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 108010021119 Trichosanthin Proteins 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- MKBUQYWFFBCMFG-UHFFFAOYSA-N acetic acid propane-1,1-diamine Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CCC(N)N MKBUQYWFFBCMFG-UHFFFAOYSA-N 0.000 description 1
- XVIYCJDWYLJQBG-UHFFFAOYSA-N acetic acid;adamantane Chemical compound CC(O)=O.C1C(C2)CC3CC1CC2C3 XVIYCJDWYLJQBG-UHFFFAOYSA-N 0.000 description 1
- RUSUZAGBORAKPY-UHFFFAOYSA-N acetic acid;n'-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.NCCNCCNCCN RUSUZAGBORAKPY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 235000019416 cholic acid Nutrition 0.000 description 1
- 229960002471 cholic acid Drugs 0.000 description 1
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- HBGGBCVEFUPUNY-UHFFFAOYSA-N cyclododecanamine Chemical compound NC1CCCCCCCCCCC1 HBGGBCVEFUPUNY-UHFFFAOYSA-N 0.000 description 1
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 1
- INCWXJJLDMUTOS-UHFFFAOYSA-N decan-1-amine nonan-1-amine Chemical compound C(CCCCCCCCC)N.C(CCCCCCCC)N INCWXJJLDMUTOS-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 229960003964 deoxycholic acid Drugs 0.000 description 1
- IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical compound CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 description 1
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 1
- WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 description 1
- 229950004394 ditiocarb Drugs 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- ZZGUZQXLSHSYMH-UHFFFAOYSA-N ethane-1,2-diamine;propanoic acid Chemical compound NCCN.CCC(O)=O.CCC(O)=O ZZGUZQXLSHSYMH-UHFFFAOYSA-N 0.000 description 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003431 steroids Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- JUKPJGZUFHCZQI-UHFFFAOYSA-N undecanoyl chloride Chemical compound CCCCCCCCCCC(Cl)=O JUKPJGZUFHCZQI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/144—Aminocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C22/00—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
- C23C22/02—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using non-aqueous solutions
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/12—Oxygen-containing compounds
- C23F11/122—Alcohols; Aldehydes; Ketones
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/167—Phosphorus-containing compounds
- C23F11/1676—Phosphonic acids
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B7/00—Insulated conductors or cables characterised by their form
- H01B7/17—Protection against damage caused by external factors, e.g. sheaths or armouring
- H01B7/28—Protection against damage caused by moisture, corrosion, chemical attack or weather
- H01B7/2806—Protection against damage caused by corrosion
-
- 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]
- Y10T428/31678—Of metal
Description
本実施例および比較例において使用した供試材料を製造元、商品名などとともに示す。また、一部のものについては、実験室にて合成したものを用いた。合成品については、以下に、その合成方法と、構造式、および、同定データを示す。また、製造元、商品名の記載がないものは、試薬を用いたものである。
・化合物A(式(2)の化合物)の合成
エチレンジアミン四酢酸二無水物5g(19.5mmol)をトルエン50mLに溶解し、更にオクタデシルアルコール5.3g(19.6mmol)を溶解する。混合液を常温にて5時間攪拌後、温度を80℃に上げ、更に1時間攪拌する。反応終了後、反応液を氷浴にて冷却攪拌しながら、純水200mLを少しずつ加える。その後常温に戻し1時間攪拌後、トルエン相を分離し減圧濃縮する。濃縮物にメタノール、水を続けて加え析出物をろ取し淡黄色の粉末を得る。この粉末をメタノールにて再結晶し、再びろ取して淡黄色の目的物を得た(収率65%)。1H−NMR(DMSO)σppm(TMS):0.85(t,3H)、1.25(m,32H)、1.55(t,2H)、2.79(m,4H)、3.47(m、,11H)、4.03(t,2H)。IR(cm−1):2925(C−H伸縮)、1734(エステルのC=O伸縮)、1460(カルボン酸のC−O伸縮)、1225(エステルのC−O伸縮)、1060(C−N伸縮)。
ジエチレントリアミン五酢酸二無水物5g(14.0mmol)をトルエン50mLに溶解し、更にドコサノール4.6g(14.0mmol)を溶解する。混合液を常温にて5時間攪拌後、温度を80℃に上げ、更に1時間攪拌する。反応終了後、反応液を氷浴にて冷却攪拌しながら、純水200mLを少しずつ加える。その後常温に戻し1時間攪拌後、トルエン相を分離し減圧濃縮する。濃縮物にメタノール、水を続けて加え析出物をろ取し淡黄色の粉末を得る。この粉末をメタノールにて再結晶し、再びろ取して淡黄色の目的物を得た(収率56%)。1H−NMR(DMSO)σppm(TMS):0.86(t,3H)、1.25(m,40H)、1.57(t,2H)、2.79(m,8H)、3.37(s,2H)、3.41(m,6H)、3.49(s,2H)、4.04(t,2H)。IR(cm−1):2910(C−H伸縮)、1734(エステルのC=O伸縮)、1455(カルボン酸のC−O伸縮)、1225(エステルのC−O伸縮)、1070(C−N伸縮)。
tert−ブチルアセトアセテート5g(31.6mmol)とオクタデシルアルコール8.5g(31.4mmol)をトルエン50mLに溶解し、攪拌しながら110℃まで加温し、副生成物のtert−ブタノールをDean−Starkトラップにて除きながら2時間反応させる。反応終了後、減圧濃縮し、白色のワックス状組成物を得る。そこに冷水20mLを加え固化させ、ろ取し目的物を得た(収率75%)。1H−NMR(CDCl3)σppm(TMS):0.89(t,3H)、1.26(m,32H)、1.64(m,2H)、2.27(s,3H)、3.44(s,2H)、4.13(t,2H)。IR(cm−1):2924(C−H伸縮)、1745、1720(βジケトン、エノール体)、1642(βジケトン、エノール体)、1420(カルボン酸のC−O伸縮)。
オクタデシルアルコールに代えて、ドコサノール10.3g(31.5mmol)を用いたこと以外、化合物Cと同様にして合成した(収率78%)。1H−NMR(CDCl3)σppm(TMS):0.89(t,3H)、1.27(m,40H)、1.64(m,2H)、2.25(s,3H)、3.44(s,2H)、4.10(t,2H)。IR(cm−1):2922(C−H伸縮)、1745、1721(βジケトン、エノール体)、1650(βジケトン、エノール体)、1425(カルボン酸のC−O伸縮)。
ヒドロキシエチルイミノ二酢酸5g(28.2mmol)をDMF200mLに溶解し、水浴にて冷却攪拌しながら、ステアロイルクロライド8.6g(28.4mmol)を少しずつ加える。その後、常温にて12時間攪拌を続ける。反応終了後、反応液を氷浴にて冷却攪拌しながら、純水200mLを少しずつ加える。その後常温に戻し1時間攪拌後、1Nの水酸化ナトリウム溶液にてpHを2.0に調整し、それらの混合液を濃縮する。得られた褐色オイルに純水200mLを加え、デカンテーションにて2回洗浄する。洗浄物を熱メタノールに溶解し冷却して再結晶させ、ろ取して淡黄色の粉末を得る。前記メタノール再結晶をもう一回繰り返して淡黄色の目的物を得た(収率67%)。1H−NMR(DMSO)σppm(TMS):0.86(t,3H)、1.24(m,30H)、1.57(t,2H)、2.34(t,2H)、2.44(t,2H)、3.48(m,6H)、4.03(t,2H)。IR(cm−1):2923(C−H伸縮)、1730(エステルのC=O伸縮)、1455(カルボン酸のC−O伸縮)、1220(エステルのC−O伸縮)、1058(C−N伸縮)。
ヒドロキシエチルイミノ二酢酸に代えて、N−(2-ヒドロキシエチル)エチレンジアミン三酢酸7.9g(28.4mmol)を用いたこと以外、化合物Eと同様にして合成した(収率51%)。1H−NMR(DMSO)σppm(TMS):0.87(t,3H)、1.24(m,30H)、1.57(t,2H)、2.37(t,2H)、2.48(t,2H)、3.45(m,9H)、4.02(t,2H)。IR(cm−1):2925(C−H伸縮)、1733(エステルのC=O伸縮)、1453(カルボン酸のC−O伸縮)、1220(エステルのC−O伸縮)、1060(C−N伸縮)。
ヒドロキシエチルイミノ二酢酸に代えて、ジアミノプロパノール四酢酸9.2g(28.5mmol)を用いたこと以外、化合物Eと同様にして合成した。(収率47%)。1H−NMR(DMSO)σppm(TMS):0.85(t,3H)、1.24(m,30H)、1.56(t,2H)、2.56(m,2H)、2.75(m,2H)、3.45(m,8H)、3.87(m),1H)、4.02(t,2H)。IR(cm−1):2922(C−H伸縮)、1735(エステルのC=O伸縮)、1453(カルボン酸のC−O伸縮)、1220(エステルのC−O伸縮)、1060(C−N伸縮)。
ヒドロキシエチルイミノ二酢酸に代えて、1−ヒドロキシエタン−1,1−ビスホスホン酸5.9g(28.6mmol)を用いたこと以外、化合物Eと同様にして合成した。(収率54%)。1H−NMR(DMSO)σppm(TMS):0.87(t,3H)、1.24(m,30H)、1.49(s,3H)、1.61(t,2H)、4.00(t,2H)。IR(cm−1):2925(C−H伸縮)、1730(エステルのC=O伸縮)、1450(C−O伸縮)、1151(P−O伸縮)、925(P−OH)。
オクタデシルアルコールに代えて、下記式(14)に示す構造を有するコレステロール7.5g(19.4mmol)を用いたこと以外、化合物Aと同様にして合成した。(収率59%)。1H−NMR(DMSO)σppm(TMS):0.5〜2.0(m,41H)、2.28(m,2H)、3.47(m,11H)、3.52(m,12H)、5.35(m,1H)。IR(cm−1):2925(C−H伸縮)、1734(エステルのC=O伸縮)、1460(カルボン酸のC−O伸縮)、1225(エステルのC−O伸縮)、1060(C−N伸縮)。
ドコサノールに代えて、下記式(15)に示す構造を有する1−アダマンタノール2.1g(13.8mmol)を用いたこと以外、化合物Bと同様にして合成した(収率48%)。1H−NMR(DMSO)σppm(TMS):1.71(m,12H)、2.14(m,3H)、2.79(m,8H)、3.36(s,2H)、3.50(m,6H)。IR(cm−1):2954、2922(C−H伸縮)、1735(エステルのC=O伸縮)、1455(カルボン酸のC−O伸縮)、1225(エステルのC−O伸縮)、1070(C−N伸縮)。
オクタデシルアルコールに代えて、下記式(14)に示す構造を有するコレステロール12.1g(31.3mmol)を用いたこと以外、化合物Cと同様にして合成した。(収率48%)。1H−NMR(CDCl3)σppm(TMS):0.5〜2.0(m,41H)、2.28(m,2H)、2.26(s,3H)、3.41(s,2H)、3.52(m,1H)、5.35(m,1H)。IR(cm−1):2925(C−H伸縮)、1745、1720(βジケトン、エノール体)、1642(βジケトン、エノール体)、1440(カルボン酸のC−O伸縮)。
オクタデシルアルコールに代えて、下記式(15)に示す構造を有する1−アダマンタノール4.8g(31.5mmol)を用いたこと以外、化合物Cと同様にして合成した(収率48%)。1H−NMR(CDCl3)σppm(TMS):1.71(m,12H)、2.14(m,3H)、2.25(s,3H)、3.44(s,2H)。IR(cm−1):2930(C−H伸縮)、1745、1722(βジケトン、エノール体)、1645(βジケトン、エノール体)、1444(カルボン酸のC−O伸縮)
・ワックス<1>[日本精蝋(株)製、商品名「LUVAX 1151」]
・ワックス<2>[ヘキスト社製、商品名「セリダスト 3620」]
・オイル[出光興産(株)製、商品名「ダフニーメカニックオイル10」]
・イソプロピルアルコール(IPA)(試薬)
上記方法により合成した各化合物A〜Lを、それぞれ、エタノール洗浄済みの各アルミニウム板(10×10×0.5mm)の上に1mgずつ乗せ、5分間100℃に加温し、融解させ流動性を高めることによって均一に塗布した。その後加温を解き、室温まで自然冷却して各サンプル片とした。
上記各サンプル片の防錆剤塗布面に中性の5%食塩水を10uL滴下し、5%食塩水が表面にスポットされたものを80℃、95%RH、50時間〜200時間という条件で高温高湿試験を行い、一定時間試験後、純水にて表面を洗浄して、サンプル片の塩水スポット箇所の表面状態の観察を行ない、白錆発生の有無を調べた。この際、当該箇所表面の写真を撮り、防錆剤塗布面全体に対する白錆発生面積率を求めた。その結果、白錆の発生がなかったものを「◎」とし、白錆の発生があったものの、白錆発生面積率が5%未満である場合を「○+」、白錆発生面積率が5%以上10%未満である場合を「○」、白錆発生面積率が10%以上25%未満である場合を「○−」、白錆発生面積率が25%以上50%未満である場合を「△」、白錆発生面積率が50%以上である場合を「×」とした。防錆試験の結果は表1の通りである。
ステアロイルクロライドに代えて、ノナデカン酸クロライド9.0g(28.4mmol)を用いたこと以外、化合物Eと同様にして合成した(収率70%)。1H−NMR(DMSO)σppm(TMS):0.86(t,3H)、1.25(m,32H)、1.58(t,2H)、2.34(t,2H)、2.44(t,2H)、3.48(m,6H)、4.03(t,2H)。IR(cm−1):2923(C−H伸縮)、1733(エステルのC=O伸縮)、1455(カルボン酸のC−O伸縮)、1220(エステルのC−O伸縮)、1056(C−N伸縮)。
トリエチレンテトラミン4.1g(28.0mmol)をDMF200mlに溶解し、水浴にて冷却攪拌しながら、ステアロイルクロライド8.6g(28.4mmol)を少しずつ加えた。その後、常温にて12時間攪拌を続けた。反応終了後、反応液を氷浴にて冷却攪拌しながら、純水500mlを少しずつ加えた。その後、常温に戻して1時間攪拌後、1Nの水酸化ナトリウム溶液を少しずつ加えていくと、pH11.0付近で褐色オイルが現れた。上澄みを除き、得られたオイルに純水を加え、デカンテーションにて2回洗浄した。洗浄物を熱メタノールに溶解し冷却して再結晶させ、ろ取して黄色の粉末を得た。メタノール再結晶をもう一回繰り返して淡黄色の目的物を得た(収率58%)。1H−NMR(DMSO)σppm(TMS):0.85(t,3H)、1.30(m,30H)、1.39(t,2H)、2.28〜2.81(m,12H)、3.60(m,5H)。IR(cm−1):3405(N−H伸縮)、2920(C−H伸縮)、1662(アミドのC=O伸縮)、1590(N−H変角)、1050(C−N伸縮)。
・化合物P:エチレンジアミン四酢酸
・化合物Q:ポリリン酸
・化合物R:ジエチレントリアミン
防錆剤が目的の塗布面以外の部分に付着した場合において、腐食等の影響が考えられる場合としては、有機材料や皮膚に付着した場合を挙げることができる。これらの表面状態としては、脂溶性、水溶性の場合が考えられる。また、水や油状成分によって湿っている場合が考えられる。そこで、その両方の状態を兼ね備えた表面状態を想定し、イソプロピルアルコール:純水=1:1の混合液を浸したろ紙を作製して、その表面に、表3に記載の各化合物をそれぞれ0.5mgずつ乗せて、1分間常温で放置後、各化合物が接触しているろ紙の接触表面におけるpHをそれぞれ測定した。この際、上記ろ紙にはユニバーサルpH試験紙(長さ5cm、幅7mm、アドバンテック社製)を用い、接触表面における色の変化によってpH値を求めた。すなわち、標準色との比較によってpH値を求めた。その結果を表3に示す。
Claims (2)
- 炭素数5〜100の長鎖アルキル基および炭素数5〜100の環状アルキル基から選択された1種または2種以上の疎水基と、ポリリン酸、アミノカルボン酸、1,3−ジケトン、アセト酢酸(エステル)、ホスホン酸から選択された1種または2種以上のキレート配位子に由来するキレート基と、がエステル結合またはエーテル結合を介して結合された、分子量が100〜1500の範囲内の、分子構造中に疎水基とキレート基とを有する化合物、を含有し、アルミニウム、鉄、銅、アルミニウム合金、鉄合金、および、銅合金から選択された1種または2種以上の金属よりなる金属材の表面に塗布するものであることを特徴とする防錆剤。
- アルミニウム、鉄、銅、アルミニウム合金、鉄合金、および、銅合金から選択された1種または2種以上の金属よりなる金属材の表面に、請求項1に記載の防錆剤が含有する分子構造中に疎水基とキレート基とを有する化合物の前記キレート基が結合し、前記疎水基は前記金属材の外側に配置されることを特徴とする表面処理金属材。
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008303887A JP5914907B2 (ja) | 2008-08-11 | 2008-11-28 | 防錆剤および表面処理金属材 |
RU2011108982/02A RU2470094C2 (ru) | 2008-08-11 | 2009-07-02 | Ингибитор коррозии и металлический материал с обработанной поверхностью |
CN200980117196XA CN102027159A (zh) | 2008-08-11 | 2009-07-02 | 防锈剂和表面处理金属材料 |
EP09806612.9A EP2333135B1 (en) | 2008-08-11 | 2009-07-02 | Rust inhibitor and surface-treated metal material |
PCT/JP2009/062084 WO2010018716A1 (ja) | 2008-08-11 | 2009-07-02 | 防錆剤および表面処理金属材 |
US12/922,464 US20110008634A1 (en) | 2008-08-11 | 2009-07-02 | Rust inhibitor and surface treatment metal material |
BRPI0906551-2A BRPI0906551A2 (pt) | 2008-08-11 | 2009-07-02 | Inibidor de ferrugem e material metálico para o tratamento de superficie. |
KR1020107023207A KR101232986B1 (ko) | 2008-08-11 | 2009-07-02 | 방청제 및 표면 처리 금속재 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008206523 | 2008-08-11 | ||
JP2008206523 | 2008-08-11 | ||
JP2008303887A JP5914907B2 (ja) | 2008-08-11 | 2008-11-28 | 防錆剤および表面処理金属材 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010065315A JP2010065315A (ja) | 2010-03-25 |
JP5914907B2 true JP5914907B2 (ja) | 2016-05-11 |
Family
ID=41668863
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008303887A Active JP5914907B2 (ja) | 2008-08-11 | 2008-11-28 | 防錆剤および表面処理金属材 |
Country Status (8)
Country | Link |
---|---|
US (1) | US20110008634A1 (ja) |
EP (1) | EP2333135B1 (ja) |
JP (1) | JP5914907B2 (ja) |
KR (1) | KR101232986B1 (ja) |
CN (1) | CN102027159A (ja) |
BR (1) | BRPI0906551A2 (ja) |
RU (1) | RU2470094C2 (ja) |
WO (1) | WO2010018716A1 (ja) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11624115B2 (en) | 2010-05-12 | 2023-04-11 | Sio2 Medical Products, Inc. | Syringe with PECVD lubrication |
US9878101B2 (en) | 2010-11-12 | 2018-01-30 | Sio2 Medical Products, Inc. | Cyclic olefin polymer vessels and vessel coating methods |
CN102747372B (zh) * | 2011-04-22 | 2014-09-17 | 比亚迪股份有限公司 | 一种铜保护剂及其制备方法和铜的保护方法 |
EP2583986A1 (en) | 2011-10-17 | 2013-04-24 | Cytec Surface Specialties, S.A. | Fluorinated water-oil repellency agents |
EP2631254A1 (en) | 2012-02-27 | 2013-08-28 | Cytec Surface Specialties, S.A. | Fluorinated water-oil repellency agents |
EP2776603B1 (en) | 2011-11-11 | 2019-03-06 | SiO2 Medical Products, Inc. | PASSIVATION, pH PROTECTIVE OR LUBRICITY COATING FOR PHARMACEUTICAL PACKAGE, COATING PROCESS AND APPARATUS |
US11116695B2 (en) | 2011-11-11 | 2021-09-14 | Sio2 Medical Products, Inc. | Blood sample collection tube |
US9554968B2 (en) | 2013-03-11 | 2017-01-31 | Sio2 Medical Products, Inc. | Trilayer coated pharmaceutical packaging |
CN103422085A (zh) * | 2012-05-22 | 2013-12-04 | 广州市泓硕环保科技有限公司 | 一种改善铁或铝基材料对涂料附着力的处理方法及组合物 |
US9764093B2 (en) | 2012-11-30 | 2017-09-19 | Sio2 Medical Products, Inc. | Controlling the uniformity of PECVD deposition |
JP6090782B2 (ja) * | 2013-02-18 | 2017-03-08 | 株式会社オートネットワーク技術研究所 | 電気接続構造及び端子 |
DE112014000872B4 (de) * | 2013-02-18 | 2023-07-20 | Autonetworks Technologies, Ltd. | Elektrische Verbindungsstruktur und Anschluss |
EP3122917B1 (en) | 2014-03-28 | 2020-05-06 | SiO2 Medical Products, Inc. | Antistatic coatings for plastic vessels |
EP3275572A4 (en) | 2015-03-26 | 2018-11-14 | Mitsui Mining and Smelting Co., Ltd. | Copper powder and conductive composition containing same |
EP3288990B1 (en) * | 2015-04-28 | 2022-09-28 | Rohm and Haas Electronic Materials LLC | Reaction products of bisanhydrids and diamines as additives for electroplating baths |
WO2017031354A2 (en) | 2015-08-18 | 2017-02-23 | Sio2 Medical Products, Inc. | Pharmaceutical and other packaging with low oxygen transmission rate |
WO2018138928A1 (ja) * | 2017-01-30 | 2018-08-02 | Jx金属株式会社 | 表面処理めっき材、コネクタ端子、コネクタ、ffc端子、ffc、fpc及び電子部品 |
KR101922000B1 (ko) * | 2017-08-14 | 2019-02-20 | 주식회사 이엔에스코리아 | 젤형 중성 세관제 조성물 및 그 조성물의 제조 방법 |
SG11202001163UA (en) * | 2017-08-30 | 2020-03-30 | Ecolab Usa Inc | Molecules having one hydrophobic group and two identical hydrophilic ionic groups and compositions thereof |
US11292734B2 (en) | 2018-08-29 | 2022-04-05 | Ecolab Usa Inc. | Use of multiple charged ionic compounds derived from poly amines for waste water clarification |
US11084974B2 (en) | 2018-08-29 | 2021-08-10 | Championx Usa Inc. | Use of multiple charged cationic compounds derived from polyamines for clay stabilization in oil and gas operations |
EP3956496A1 (en) | 2019-04-16 | 2022-02-23 | Ecolab USA Inc. | Use of multiple charged cationic compounds derived from polyamines and compositions thereof for corrosion inhibition in a water system |
CN110592595A (zh) * | 2019-09-19 | 2019-12-20 | 桂林理工大学 | 2,5-噻吩二甲醛缩2-氨基芴希夫碱缓蚀剂的制备方法及其应用 |
CN112391072B (zh) * | 2020-11-12 | 2021-10-26 | 陕西科技大学 | 一种疏水长链改性l-组氨酸缓蚀剂及其制备方法和应用 |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2325376A (en) * | 1940-08-27 | 1943-07-27 | Gen Electric | Condensation product of amidogen compounds, aldehydes, and ketoesters |
US2359407A (en) * | 1941-03-31 | 1944-10-03 | Ici Ltd | Protection of metal surfaces from corrosion |
CA718041A (en) * | 1961-04-28 | 1965-09-14 | Dexter Martin | Surface active chelating agents |
US3463835A (en) * | 1965-10-05 | 1969-08-26 | Plains Chem Dev Co | Aromatic polyphosphonic acids,salts and esters |
US3714066A (en) * | 1970-04-13 | 1973-01-30 | Monsanto Co | Methods of inhibiting corrosion with ethane diphosphonate compositions |
DE2530139C3 (de) * | 1975-04-30 | 1979-06-21 | Joh. A. Benckiser Gmbh, 6700 Ludwigshafen | N-Acyl-1 -aminoalkan-1,1 -diphosphonsäuren, deren Herstellung und Verwendung |
JPH04314895A (ja) * | 1991-04-15 | 1992-11-06 | Nikko Kyodo Co Ltd | 表面処理液及び方法 |
US5284972A (en) * | 1993-06-14 | 1994-02-08 | Hampshire Chemical Corp. | N-acyl-N,N',N'-ethylenediaminetriacetic acid derivatives and process of preparing same |
JP3148591B2 (ja) * | 1994-09-13 | 2001-03-19 | トヨタ自動車株式会社 | 溶液中に含まれる金属の分離/除去方法と分離装置 |
DE19636077A1 (de) * | 1996-09-05 | 1998-03-12 | Basf Ag | Verwendung wäßriger Polymerisatdispersionen für den Korrosionsschutz metallischer Oberflächen |
US5922790A (en) * | 1997-01-09 | 1999-07-13 | Eastman Chemical Company | Non-polymeric acetoacetates as adhesion promoting coalescing agents |
US5833741A (en) * | 1997-01-16 | 1998-11-10 | Lonza Inc. | Waterproofing and preservative compositons for wood |
FR2762016B1 (fr) * | 1997-04-11 | 1999-06-04 | Atochem Elf Sa | Utilisation de thiols contenant des groupes amino comme inhibiteurs de corrosion dans l'industrie petroliere |
JPH1116615A (ja) * | 1997-06-23 | 1999-01-22 | Tokyo Gas Co Ltd | 接続具 |
JPH11166151A (ja) * | 1997-12-01 | 1999-06-22 | Nkk Corp | 耐食性に優れた表面処理鋼板 |
DE19757302A1 (de) * | 1997-12-22 | 1999-07-01 | Siemens Ag | Beschichtung von Metalloberflächen insbesondere für die Mikroelektronik |
JP2000160371A (ja) * | 1998-11-30 | 2000-06-13 | Chubu Kiresuto Kk | AlまたはAl合金粉末の腐食抑制剤及び腐食抑制法、並びにAlまたはAl合金含有塗料 |
US6596393B1 (en) * | 2000-04-20 | 2003-07-22 | Commscope Properties, Llc | Corrosion-protected coaxial cable, method of making same and corrosion-inhibiting composition |
US6572789B1 (en) * | 2001-04-02 | 2003-06-03 | Ondeo Nalco Company | Corrosion inhibitors for aqueous systems |
EP1394289B1 (en) * | 2001-04-06 | 2012-05-09 | Nippon Oil Corporation | Rust-preventive oil composition |
TWI297102B (en) * | 2001-08-03 | 2008-05-21 | Nec Electronics Corp | Removing composition |
US7855130B2 (en) * | 2003-04-21 | 2010-12-21 | International Business Machines Corporation | Corrosion inhibitor additives to prevent semiconductor device bond-pad corrosion during wafer dicing operations |
US7524535B2 (en) * | 2004-02-25 | 2009-04-28 | Posco | Method of protecting metals from corrosion using thiol compounds |
JP5255764B2 (ja) * | 2006-12-28 | 2013-08-07 | 株式会社オートネットワーク技術研究所 | 被覆電線およびワイヤーハーネス |
US7972655B2 (en) * | 2007-11-21 | 2011-07-05 | Enthone Inc. | Anti-tarnish coatings |
-
2008
- 2008-11-28 JP JP2008303887A patent/JP5914907B2/ja active Active
-
2009
- 2009-07-02 WO PCT/JP2009/062084 patent/WO2010018716A1/ja active Application Filing
- 2009-07-02 US US12/922,464 patent/US20110008634A1/en not_active Abandoned
- 2009-07-02 CN CN200980117196XA patent/CN102027159A/zh active Pending
- 2009-07-02 BR BRPI0906551-2A patent/BRPI0906551A2/pt not_active IP Right Cessation
- 2009-07-02 KR KR1020107023207A patent/KR101232986B1/ko active IP Right Grant
- 2009-07-02 EP EP09806612.9A patent/EP2333135B1/en active Active
- 2009-07-02 RU RU2011108982/02A patent/RU2470094C2/ru active
Also Published As
Publication number | Publication date |
---|---|
EP2333135A4 (en) | 2014-06-04 |
BRPI0906551A2 (pt) | 2015-07-07 |
US20110008634A1 (en) | 2011-01-13 |
WO2010018716A1 (ja) | 2010-02-18 |
EP2333135B1 (en) | 2018-01-03 |
KR20100130997A (ko) | 2010-12-14 |
CN102027159A (zh) | 2011-04-20 |
RU2470094C2 (ru) | 2012-12-20 |
EP2333135A1 (en) | 2011-06-15 |
JP2010065315A (ja) | 2010-03-25 |
KR101232986B1 (ko) | 2013-02-13 |
RU2011108982A (ru) | 2012-09-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5914907B2 (ja) | 防錆剤および表面処理金属材 | |
JP5633665B2 (ja) | 防錆剤および表面処理金属材 | |
JP2011099152A (ja) | 防錆剤、防錆皮膜および表面処理金属材 | |
US20060269760A1 (en) | Corrosion-resistant metal surfaces | |
JP7114806B2 (ja) | 防錆剤、防錆剤組成物、被膜形成材、被膜、及び金属部品 | |
JP2010174340A (ja) | 防錆剤および表面処理金属材 | |
US4626283A (en) | Corrosion and marine growth inhibiting compositions | |
CN104718315A (zh) | 脂族二羧酸混合物调配物 | |
JP2010144205A (ja) | 防錆剤および表面処理金属材 | |
JPS62502467A (ja) | シラン組成物 | |
JPS63291965A (ja) | 金属表面被覆用組成物 | |
JP2604396B2 (ja) | 金属の腐食防止方法 | |
JP6727649B2 (ja) | 金属腐食抑制剤及びそれを用いた金属腐食抑制方法 | |
JPS5947033B2 (ja) | ヒドロキシ多塩基酸塩型防錆剤 | |
JP2004059497A (ja) | 新規イミダゾールアルコール化合物及びその製造方法並びにそれを用いる表面処理剤 | |
JPS6056434B2 (ja) | 防錆剤の製造法 | |
JPH02178373A (ja) | 加水分解型シリコーン樹脂被膜を有する塗装物 | |
LEROY | Polythioglycolate passivation of zinc | |
JP2021143419A (ja) | 防錆剤、防錆剤組成物、被膜形成材、被膜、及び金属部品 | |
CN103589490B (zh) | 长效环保防锈油 | |
JP2016030777A (ja) | シリカ質皮膜形成用処理液 | |
JP4578122B2 (ja) | 親油性キレート剤の製法 | |
JP2006513264A (ja) | 金属表面処理用の疎水性−親水性化合物 | |
JP3585394B2 (ja) | 新規トリカルボニル化合物およびその製造方法並びにそれを用いる金属防錆剤 | |
JP2006045643A (ja) | 気化性防錆紙用防錆剤組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20111122 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20111122 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130903 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131029 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20140401 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140519 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20140602 |
|
A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20140620 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150520 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20151023 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20151204 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160310 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5914907 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |