CA1250496A - Polymere chelateurs pour modifier les proprietes d'une surface metallique - Google Patents

Polymere chelateurs pour modifier les proprietes d'une surface metallique

Info

Publication number: CA1250496A
Authority: CA; Canada
Prior art keywords: chelating; metal; polymer; lower alkyl; groups
Prior art date: 1985-01-08
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.): Expired

Application number

CA000471643A

Other languages

English (en)

Inventor

David R. Whitcomb

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

3M Co

Original Assignee

Minnesota Mining and Manufacturing Co

Priority date (The priority date 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 date listed.)

1985-01-08

Filing date

1985-01-08

Publication date

1989-02-28

1985-01-08 Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co

1985-01-08 Priority to CA000471643A priority Critical patent/CA1250496A/fr

1989-02-28 Application granted granted Critical

1989-02-28 Publication of CA1250496A publication Critical patent/CA1250496A/fr

Status Expired legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 111
229910052751 metal Inorganic materials 0.000 title claims abstract description 107
239000002184 metal Substances 0.000 title claims abstract description 106
239000000178 monomer Substances 0.000 claims abstract description 81
125000000217 alkyl group Chemical group 0.000 claims abstract description 44
229920001577 copolymer Polymers 0.000 claims abstract description 41
238000000034 method Methods 0.000 claims abstract description 20
125000004429 atom Chemical group 0.000 claims abstract description 13
239000002131 composite material Substances 0.000 claims abstract description 13
150000002500 ions Chemical class 0.000 claims abstract description 11
239000001257 hydrogen Substances 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
238000000576 coating method Methods 0.000 claims description 36
239000011248 coating agent Substances 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 18
239000013522 chelant Substances 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 15
229910021645 metal ion Inorganic materials 0.000 claims description 14
238000012360 testing method Methods 0.000 claims description 14
150000002739 metals Chemical class 0.000 claims description 11
125000004957 naphthylene group Chemical group 0.000 claims description 10
-1 phenylene, phenylene Chemical group 0.000 claims description 9
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
229920005604 random copolymer Polymers 0.000 claims description 7
229910045601 alloy Inorganic materials 0.000 claims description 6
239000000956 alloy Substances 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
230000009471 action Effects 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
230000000379 polymerizing effect Effects 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
238000009472 formulation Methods 0.000 claims description 4
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238000001179 sorption measurement Methods 0.000 claims description 4
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238000001035 drying Methods 0.000 claims description 3
229910000000 metal hydroxide Inorganic materials 0.000 claims description 3
150000004692 metal hydroxides Chemical class 0.000 claims description 3
229910052723 transition metal Inorganic materials 0.000 claims description 3
150000003624 transition metals Chemical class 0.000 claims description 3
239000002245 particle Substances 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 2
229910052698 phosphorus Inorganic materials 0.000 claims 2
238000004090 dissolution Methods 0.000 claims 1
239000000725 suspension Substances 0.000 claims 1
229920001519 homopolymer Polymers 0.000 abstract description 10
230000037452 priming Effects 0.000 abstract description 4
238000007385 chemical modification Methods 0.000 abstract description 2
239000011253 protective coating Substances 0.000 abstract description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
229910000831 Steel Inorganic materials 0.000 description 15
239000010959 steel Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
229910001868 water Inorganic materials 0.000 description 14
229910052782 aluminium Inorganic materials 0.000 description 13
238000010348 incorporation Methods 0.000 description 13
239000004922 lacquer Substances 0.000 description 13
239000000047 product Substances 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 12
239000010410 layer Substances 0.000 description 12
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 11
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
230000006872 improvement Effects 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
238000011282 treatment Methods 0.000 description 9
239000000853 adhesive Substances 0.000 description 8
230000001070 adhesive effect Effects 0.000 description 8
239000002738 chelating agent Substances 0.000 description 8
239000002253 acid Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000003973 paint Substances 0.000 description 7
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
150000002430 hydrocarbons Chemical group 0.000 description 6
239000004816 latex Substances 0.000 description 6
229920000126 latex Polymers 0.000 description 6
239000000463 material Substances 0.000 description 6
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
229910002706 AlOOH Inorganic materials 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
229910019142 PO4 Inorganic materials 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
238000005260 corrosion Methods 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
239000010452 phosphate Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000005725 8-Hydroxyquinoline Substances 0.000 description 4
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
238000007334 copolymerization reaction Methods 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
239000010949 copper Substances 0.000 description 4
230000007797 corrosion Effects 0.000 description 4
238000005238 degreasing Methods 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229960003540 oxyquinoline Drugs 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
229960004889 salicylic acid Drugs 0.000 description 4
YNFBMDWHEHETJW-UHFFFAOYSA-N 2-pyridin-2-yl-1h-benzimidazole Chemical compound N1=CC=CC=C1C1=NC2=CC=CC=C2N1 YNFBMDWHEHETJW-UHFFFAOYSA-N 0.000 description 3
VRLXQFXFASUPJO-UHFFFAOYSA-N 3-(2-chloroacetyl)oxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOC(=O)CCl VRLXQFXFASUPJO-UHFFFAOYSA-N 0.000 description 3
229910001369 Brass Inorganic materials 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
230000008901 benefit Effects 0.000 description 3
239000010951 brass Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000284 extract Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
229910015400 FeC13 Inorganic materials 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
229910001209 Low-carbon steel Inorganic materials 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
239000002262 Schiff base Substances 0.000 description 2
150000004753 Schiff bases Chemical group 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229920001400 block copolymer Polymers 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
108010088172 chelatin Proteins 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 description 2
229940000425 combination drug Drugs 0.000 description 2
239000000356 contaminant Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000000875 corresponding effect Effects 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
LNTHITQWFMADLM-UHFFFAOYSA-M gallate Chemical compound OC1=CC(C([O-])=O)=CC(O)=C1O LNTHITQWFMADLM-UHFFFAOYSA-M 0.000 description 2
229920000578 graft copolymer Polymers 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
150000002466 imines Chemical class 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
229920001897 terpolymer Polymers 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
IBALVVJJRIOXHH-UHFFFAOYSA-N (3-formyl-4-hydroxyphenyl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=C(O)C(C=O)=C1 IBALVVJJRIOXHH-UHFFFAOYSA-N 0.000 description 1
DCNCKFLANOGBGV-UHFFFAOYSA-N (4-amino-3-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(N)C(O)=C1 DCNCKFLANOGBGV-UHFFFAOYSA-N 0.000 description 1
IKHWZYDHACDIKL-UHFFFAOYSA-N (7-iodo-2-quinolin-2-ylquinolin-8-yl) prop-2-enoate Chemical compound C1=CC=CC2=NC(C=3C=CC4=CC=C(C(=C4N=3)OC(=O)C=C)I)=CC=C21 IKHWZYDHACDIKL-UHFFFAOYSA-N 0.000 description 1
DMDRFFLGPYHJKF-UHFFFAOYSA-N (8-hydroxy-4-nitroquinolin-5-yl) 2-methylprop-2-enoate Chemical compound C1=CC([N+]([O-])=O)=C2C(OC(=O)C(=C)C)=CC=C(O)C2=N1 DMDRFFLGPYHJKF-UHFFFAOYSA-N 0.000 description 1
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
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
JDUUBUKAOYURMC-UHFFFAOYSA-N 2-(2-chloroacetyl)oxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)CCl JDUUBUKAOYURMC-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
QIYHCQVVYSSDTI-UHFFFAOYSA-N 2-(phenyliminomethyl)phenol Chemical compound OC1=CC=CC=C1C=NC1=CC=CC=C1 QIYHCQVVYSSDTI-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
YPMKNVUPBWJVPU-UHFFFAOYSA-N 2-hydroxy-2-[4-(2-methylprop-2-enoylamino)phenyl]acetic acid Chemical compound CC(=C)C(=O)NC1=CC=C(C(O)C(O)=O)C=C1 YPMKNVUPBWJVPU-UHFFFAOYSA-N 0.000 description 1
CSECHWHAAUMBAK-UHFFFAOYSA-N 2-hydroxy-2-[4-(2-methylprop-2-enoyloxy)phenyl]acetic acid Chemical compound CC(=C)C(=O)OC1=CC=C(C(O)C(O)=O)C=C1 CSECHWHAAUMBAK-UHFFFAOYSA-N 0.000 description 1
LOOIGDSYRPZXNT-UHFFFAOYSA-N 2-hydroxy-4-(2-methylprop-2-enoylamino)-5-nitrobenzoic acid Chemical compound CC(=C)C(=O)NC1=CC(O)=C(C(O)=O)C=C1[N+]([O-])=O LOOIGDSYRPZXNT-UHFFFAOYSA-N 0.000 description 1
JYLCVRHQTJPCTN-UHFFFAOYSA-N 2-hydroxy-4-(2-methylprop-2-enoylamino)benzoic acid Chemical compound CC(=C)C(=O)NC1=CC=C(C(O)=O)C(O)=C1 JYLCVRHQTJPCTN-UHFFFAOYSA-N 0.000 description 1
BUFBLQXPZFSNRC-UHFFFAOYSA-N 2-hydroxy-4-(prop-2-enoylamino)benzoic acid Chemical compound OC(=O)C1=CC=C(NC(=O)C=C)C=C1O BUFBLQXPZFSNRC-UHFFFAOYSA-N 0.000 description 1
IAQMTLHYQOOBPY-UHFFFAOYSA-N 2-hydroxy-4-prop-2-enoyloxybenzoic acid Chemical compound OC(=O)C1=CC=C(OC(=O)C=C)C=C1O IAQMTLHYQOOBPY-UHFFFAOYSA-N 0.000 description 1
WPTCSQBWLUUYDV-UHFFFAOYSA-N 2-quinolin-2-ylquinoline Chemical class C1=CC=CC2=NC(C3=NC4=CC=CC=C4C=C3)=CC=C21 WPTCSQBWLUUYDV-UHFFFAOYSA-N 0.000 description 1
GDTSJMKGXGJFGQ-UHFFFAOYSA-N 3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B([O-])OB2OB([O-])OB1O2 GDTSJMKGXGJFGQ-UHFFFAOYSA-N 0.000 description 1
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HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
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125000004434 sulfur atom Chemical group 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
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235000018553 tannin Nutrition 0.000 description 1
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
239000004753 textile Substances 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
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HLCHESOMJVGDSJ-UHFFFAOYSA-N thiq Chemical compound C1=CC(Cl)=CC=C1CC(C(=O)N1CCC(CN2N=CN=C2)(CC1)C1CCCCC1)NC(=O)C1NCC2=CC=CC=C2C1 HLCHESOMJVGDSJ-UHFFFAOYSA-N 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
238000000870 ultraviolet spectroscopy Methods 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Paints Or Removers (AREA)

CA000471643A 1985-01-08 1985-01-08 Polymere chelateurs pour modifier les proprietes d'une surface metallique Expired CA1250496A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000471643A CA1250496A (fr)	1985-01-08	1985-01-08	Polymere chelateurs pour modifier les proprietes d'une surface metallique

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000471643A CA1250496A (fr)	1985-01-08	1985-01-08	Polymere chelateurs pour modifier les proprietes d'une surface metallique

Publications (1)

Publication Number	Publication Date
CA1250496A true CA1250496A (fr)	1989-02-28

Family

ID=4129529

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000471643A Expired CA1250496A (fr)	1985-01-08	1985-01-08	Polymere chelateurs pour modifier les proprietes d'une surface metallique

Country Status (1)

Country	Link
CA (1)	CA1250496A (fr)

1985
- 1985-01-08 CA CA000471643A patent/CA1250496A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-02-28	MKEX	Expiry

Publication	Publication Date	Title
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