WO1996012054A1 - Verwendung von guanidiniumsalzen ungesättigter fettsäuren als korrosionsschutzwirkstoff - Google Patents
Verwendung von guanidiniumsalzen ungesättigter fettsäuren als korrosionsschutzwirkstoff Download PDFInfo
- Publication number
- WO1996012054A1 WO1996012054A1 PCT/EP1995/003931 EP9503931W WO9612054A1 WO 1996012054 A1 WO1996012054 A1 WO 1996012054A1 EP 9503931 W EP9503931 W EP 9503931W WO 9612054 A1 WO9612054 A1 WO 9612054A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- fatty acids
- acid
- use according
- guanidinium salts
- Prior art date
Links
- 235000021122 unsaturated fatty acids Nutrition 0.000 title claims abstract description 34
- 150000004670 unsaturated fatty acids Chemical class 0.000 title claims description 33
- 150000002357 guanidines Chemical class 0.000 title abstract description 4
- 239000013543 active substance Substances 0.000 title description 2
- 239000000839 emulsion Substances 0.000 claims abstract description 40
- 239000002904 solvent Substances 0.000 claims abstract description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- -1 unsaturated fatty acid guanidine salts Chemical class 0.000 claims abstract description 12
- 239000007764 o/w emulsion Substances 0.000 claims abstract description 7
- 235000021281 monounsaturated fatty acids Nutrition 0.000 claims abstract description 4
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims abstract description 4
- 238000005260 corrosion Methods 0.000 claims description 55
- 230000007797 corrosion Effects 0.000 claims description 51
- 239000003921 oil Substances 0.000 claims description 42
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 36
- 239000000194 fatty acid Substances 0.000 claims description 23
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 22
- 229930195729 fatty acid Natural products 0.000 claims description 22
- 150000004665 fatty acids Chemical class 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 14
- 239000002480 mineral oil Substances 0.000 claims description 12
- 235000010446 mineral oil Nutrition 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 150000001983 dialkylethers Chemical class 0.000 claims description 9
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 9
- 239000000539 dimer Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 5
- 239000005642 Oleic acid Substances 0.000 claims description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 5
- 239000004530 micro-emulsion Substances 0.000 claims description 5
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 claims description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims description 4
- 239000005662 Paraffin oil Substances 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 239000011877 solvent mixture Substances 0.000 claims description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 2
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 claims description 2
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 claims description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 2
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 235000021319 Palmitoleic acid Nutrition 0.000 claims description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- 229940114079 arachidonic acid Drugs 0.000 claims description 2
- 235000021342 arachidonic acid Nutrition 0.000 claims description 2
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 claims description 2
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 2
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 2
- 239000010696 ester oil Substances 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 2
- 229960003656 ricinoleic acid Drugs 0.000 claims description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 229960002703 undecylenic acid Drugs 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 34
- 229910001868 water Inorganic materials 0.000 abstract description 33
- 239000000243 solution Substances 0.000 description 24
- 239000012071 phase Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 239000002253 acid Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000011814 protection agent Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229940049964 oleate Drugs 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 230000001804 emulsifying effect Effects 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 229940051250 hexylene glycol Drugs 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- IMYZYCNQZDBZBQ-UHFFFAOYSA-N 9,10-epoxyoctadecanoic acid Chemical compound CCCCCCCCC1OC1CCCCCCCC(O)=O IMYZYCNQZDBZBQ-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000007957 coemulsifier Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- VACHUYIREGFMSP-UHFFFAOYSA-N (+)-threo-9,10-Dihydroxy-octadecansaeure Natural products CCCCCCCCC(O)C(O)CCCCCCCC(O)=O VACHUYIREGFMSP-UHFFFAOYSA-N 0.000 description 2
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 2
- JPFGKGZYCXLEGQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-5-methylpyrazole-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1C(C)=C(C(O)=O)C=N1 JPFGKGZYCXLEGQ-UHFFFAOYSA-N 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
- VACHUYIREGFMSP-SJORKVTESA-N 9,10-Dihydroxystearic acid Natural products CCCCCCCC[C@@H](O)[C@@H](O)CCCCCCCC(O)=O VACHUYIREGFMSP-SJORKVTESA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 238000005555 metalworking Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000005068 cooling lubricant Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002149 estolides Chemical class 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- BARWIPMJPCRCTP-UHFFFAOYSA-N oleic acid oleyl ester Natural products CCCCCCCCC=CCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC BARWIPMJPCRCTP-UHFFFAOYSA-N 0.000 description 1
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000000614 phase inversion technique Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000003799 water insoluble solvent Substances 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
-
- 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
- C23F11/146—Nitrogen-containing compounds containing a multiple nitrogen-to-carbon bond
Definitions
- the invention relates to oil-based corrosion protection agents for metallic, in particular iron-based surfaces, which are preferably used in the form of oil-in-water emulsions.
- the invention provides alkyla-free anti-corrosion agents which are characterized by good oil solubility and which at the same time cause the oil phase to be emulsified in water.
- Anti-rust emulsions are used for the temporary protection of metallic materials against atmospheric influences that cause corrosion. They contain essentially non-polar or polar oils, emulsifiers, corrosion inhibitors and water. Their effect is based on the adsorption of inhibitor molecules on the metal surface and the formation of a protective film from emulsion components, which acts as a diffusion barrier for atmospheric oxygen and water. T. Forster et al. report in "Surface-Surface", 1989, No. 4, pp. 8-12, about modes of action and methods of investigation of rust protection emulsions.
- Sulfur-containing corrosion inhibitors such as, for example, alkylarylsulfonic acids, petroleum sulfonates or salts of alkylsulfonamidocarboxylic acids have the disadvantage that they can easily be broken down by microorganisms such as sulfur-reducing bacteria, which can lead to considerable odor nuisance.
- stearic acid derivatives have been described as anti-corrosion agents (DE-C-32 03 491).
- Examples include 9,10-dihydroxystearic acid and its alkali metal salts and their oligomeric condensates, 9,10-epoxy stearic acid, their alkali metal salts and their oligomeric estolides and finally mixed oligomerizates of 9,10-epoxy and 9,10-dihydroxystearic acid .
- Corrosion protection agents which are to be used in the form of oil-in-water emulsions can be brought onto the market as purely oily, that is to say anhydrous, concentrates in order to be brought into the ready-to-use emulsion form by adding water at the point of use .
- These oil concentrates contain the corrosion inhibitors, which must therefore be oil-soluble. So that the oil concentrates spontaneously form an emulsion when diluted with water, that is, they can be self-emulsifying, it was previously necessary that these concentrates also contain emulsifiers in addition to the corrosion inhibitors.
- US Pat. No. 2,978,415 discloses guanidinium salts of unsaturated fatty acids and processes for their preparation. These guanidine soaps of unsaturated fatty acids are used as cleaning-enhancing active substances in the cleaning of textiles with solvents, that is to say in the so-called “chemical cleaning” or “dry cleaning”. For this application, which takes place in the purely organic phase, neither a corrosion protection effect nor an emuIgie ability is important. Accordingly, this US document contains no information on a corresponding effect of the guaniidine soaps of unsaturated fatty acids.
- the object of the present invention is to provide new sulfur and alkylamine-free corrosion protection agents, the oil solutions of which do not have unacceptably high viscosities even at high concentrations of the agent, and which at the same time emulsify the oil phase when mixed with water, without additional emulsifiers are required for this.
- This object is achieved by the use of guanidinium salts of mono- or polyunsaturated fatty acids with 6 to 44 carbon atoms to achieve temporary protection against corrosion on metallic, preferably iron-based surfaces.
- “Fatty acids” are understood here to mean carboxylic acids, which may be OH-substituted.
- the unsaturated fatty acids that can be used can be divided into two groups: native fatty acids, as they occur as a component of natural oils and fats, and so-called dimer fatty acids, which are technically accessible through, generally acid-catalyzed, dimerization of suitable fatty acids.
- the unsaturated fatty acids that can be used are therefore once characterized in that they are native Represent fatty acids, ie are branched or preferably linear, have one to six, preferably one to three double bonds and preferably contain 11 to 28, in particular 18 to 22, carbon atoms.
- Suitable unsaturated fatty acids of this type are preferably monobasic and, for example, selected from undecylenic acid, myristoleic acid, palmitoleic acid, oleic acid, ricinoleic acid, erucic acid, linoleic acid, linolenic acid, arachidonic acid and mixtures thereof.
- unsaturated fatty acids from the group of so-called diacids are suitable. These are polybasic, preferably dibasic. Those dimer acids which have 36 to 44 carbon atoms are particularly suitable.
- Guanidinium salts of defined, pure fatty acids can advantageously be used for the purpose according to the invention.
- guanidinium salts of technical fatty acid mixtures will be used in practice, which in addition to unsaturated fatty acids of different C chain lengths can also contain certain proportions of saturated fatty acids.
- Such technical fatty acid mixtures can be obtained, for example, by splitting suitable natural oils and fats.
- the technical fatty acid mixtures consist of at least 50% by weight, preferably at least 80% by weight, of unsaturated fatty acids of the above-mentioned carbon chain lengths.
- dimer fatty acids which can likewise be used according to the invention, generally do not represent pure substances either, but can contain fatty acids of different carbon chain lengths and / or different degrees of oligomerization.
- trimerization or polymerization products may also be present in addition to unreacted and / or isomerized mono-fatty acids. If we are talking about dimer fatty acids here, we mean product mixtures which are at least 50% by weight, preferably at least 70% by weight consist of dimer fatty acid with a C chain length between 36 and 44.
- Such products are commercially available, for example from Unichema under the product group name Pripol R or from Henkel KGaA under the product group name Empol R.
- guanidinium salts of the abovementioned fatty acids they are used as solutions in hydrocarbons which are liquid at working temperature, dialkyl ethers and / or acetals which are largely insoluble in water, and mixtures thereof.
- ester oils such as oleyl oleate, esterification products of aliphatic dicarboxylic acids (preferably C ⁇ -g) with branched Guerbet alcohols (preferably C12-20) (EP-A-489809), esters of Ci-5- Monocarboxylic acids with mono- or polyfunctional alcohols (for example described in DE-A-3907 391), esters of Cß-n-monocarboxylic acids with mono- or polyfunctional alcohols (for example described in DE-A-3907 392), and alkoxylation products of triglycerides with 0.5 - 3 mol E0 and / or PO, for example glycerol propoxylate trioleate (German patent application P 4323771).
- oil-like solvents These essentially water-insoluble solvents are further referred to as "oil-like solvents".
- Solutions which contain between 1 and 45% by weight of guanidinium salts of unsaturated fatty acids are preferably used. At lower contents, the corrosion protection effect decreases significantly, while at higher contents, the solutions generally become so highly viscous that their handling and use for the formation of emulsions is unnecessarily difficult. For the purposes of the invention, however, higher concentrations can also be used if the associated difficulties in emulsion formation are accepted, for example prior heating of concentrate and preparation water and the use of technical emulsifying aids such as, for example, fast-running toothed disks or ultrasound.
- suitable oil-like solvents for the guanidinium salts of unsaturated fatty acids are hydrocarbons which are liquid at working temperature, that is to say a temperature between about 10 and about 90 ° C.
- hydrocarbons which are liquid at working temperature, that is to say a temperature between about 10 and about 90 ° C.
- paraffin oil or mineral oil in the case of mineral oil low-aromatic mineral oils are preferred for ecological and toxicological reasons.
- Suitable oils of this type are commercially available. Examples include pioneering oil 4556 from Hansen & Rosenthal, Enerpar 3036 from Irish BP and Parex Paraffin II from Leu-na-Werke.
- dialkyl ethers can still have free hydroxyl groups and are then referred to as hydroxy ischether.
- the use of such dialkyl ethers in metalworking fluids is described, for example, in German patent application P 4237501.
- Such dialkyl ethers are commercially available, for example from Henkel KGaA under the name Cetiol-OE (dioctyl ether).
- Other suitable oil-like solvents for the use of the guani dinium salts according to the invention are acetals based on monovalent aldehydes having 1 to 25, preferably 1 to 10, carbon atoms and monohydric alcohols having 1 to 25, in particular 2 to 20, carbon atoms.
- the use of such acetals as mineral oil substitute, oil component or base oil in lubricating oils and in metalworking fluids is known from EP-A-512 501. A general regulation for the production of such acetals is also given there.
- the guanidinium salts of unsaturated fatty acids are preferably used in such a way that the solution of the guanidinium salts in one of the above-mentioned oil-like solvents or in mixtures thereof is used as the oil phase of an oil-in-water emulsion.
- the proportion of oil in the emulsion which means the solution of the guanidinium salts of the unsaturated fatty acids, in the emulsion is preferably between 0.5 and 50% by weight, in particular between 5 and 20% by weight.
- the rule of thumb here is that the proportion of the oil phase can be chosen to be lower the higher the concentration of the guaniidinium salts of unsaturated fatty acids in the oil phase.
- Suitable glycols are, for example, butyl diglycol, hexylene glycol or dipropylene glycol, which contain 1 to 10% by weight of the guanidinium salt solution.
- the glycols can either be added to the solution of the guaniidinium salts of unsaturated fatty acids in oil-like solvents or added to the oil-like solvent before the reaction of guanidinium salts of volatile acids with unsaturated fatty acids described below. Because of the beneficial effect on corrosion protection, the use of hexylene glycol is preferred.
- the invention further relates to the oil-in-water emulsions suitable for the use according to the invention of guanidinium salts of unsaturated fatty acids.
- guanidinium salts of unsaturated fatty acids can be used as cooling lubricant emulsions in metal cutting, the emulsions being able to contain further active ingredients known for this area of application, for example lubrication-enhancing additives or biocides.
- the invention comprises oil-in-water emulsions, the oil phase of which is an oil-like solvent or solvent mixture according to one or more of claims 6 to 9 and the guanidinium salts of unsaturated fatty acids according to one or more of claims 1 to 5 in concentrations of Contains 1 to 45 wt .-%, preferably 5 to 20 wt .-% dissolved with respect to the oil phase, the proportion of the oil phase in the emulsion between 0.5 and 50 preferably 5 to 20 wt .-%.
- Nonionic surfactants in particular ethoxylation products of fatty alcohols, such as, for example, an adduct of 6 moles of ethylene oxide with 1 mole of a C12 / 14-fatty alcohol mixture, or anionic emulsifiers such as, for example, alkylbenzenesulfonates, are suitable for this.
- fatty alcohols such as, for example, an adduct of 6 moles of ethylene oxide with 1 mole of a C12 / 14-fatty alcohol mixture
- anionic emulsifiers such as, for example, alkylbenzenesulfonates
- the emulsion can be in the form of a conventional, milky opaque emulsion.
- the emulsion can also be advantageous to use the emulsion in the form of an almost transparent so-called micro-emulsion with an oil content of up to 50% by weight, as can be obtained by phase inversion from a water-in-oil emulsion .
- PIT phase inversion temperature
- guanidinium salts of unsaturated fatty acids is described in the above-mentioned US Pat. No. 2,978,415.
- a mixture of unsaturated fatty acids can be dissolved in an organic solvent such as methyl isobutyl ketone and guanidinium carbonate can be added.
- an organic solvent such as methyl isobutyl ketone
- guanidinium carbonate can be added.
- the solvent and the water of reaction can be removed, leaving the product in the form of a brown, waxy paste.
- Rosion inhibitors are known, are unsuitable for the use according to the invention, since their oil solutions in the concentration ranges according to the invention are not mobile liquids, but wax-like pastes.
- Solvent dioctyl ether Cetiol-OE, Henkel KGaA.
- Example 8 Product from up to 16 days no corrosion Example 3 after 25 days termination with traces of corrosion
- a microemulsion by the phase inversion method 2.6 parts by weight of this guanidinium oleate and 0.26 part by weight of sodium citrate were dissolved in 51.04 parts by weight of water.
- the solution was mixed with 40 parts by weight of mineral oil (pioneering oil 4556) and 6.1 parts by weight of emulsifier (adduct of 4 moles of ethylene oxide with a C12 / 14- " alcohol mixture) at a temperature above that obtained by preliminary tests
- the phase inversion temperature of 35 ° C. was mixed by stirring and cooled below the phase inversion temperature, and a transparent microemulsion was obtained which could be diluted by adding water.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- Colloid Chemistry (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Paints Or Removers (AREA)
- Load-Engaging Elements For Cranes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE59505930T DE59505930D1 (de) | 1994-10-14 | 1995-10-05 | Verwendung von guanidiniumsalzen ungesättigter fettsäuren als korrosionsschutzwirkstoff |
EP95935435A EP0786019B1 (de) | 1994-10-14 | 1995-10-05 | Verwendung von guanidiniumsalzen ungesättigter fettsäuren als korrosionsschutzwirkstoff |
JP8512901A JPH10507231A (ja) | 1994-10-14 | 1995-10-05 | 腐食抑制剤としての不飽和脂肪酸のグアニジン塩の使用 |
US08/817,458 US5749947A (en) | 1994-10-14 | 1995-10-05 | Use of guanidinium salts of unsaturated fatty acids as corrosion inhibitors |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4436764.3 | 1994-10-14 | ||
DE4436764A DE4436764A1 (de) | 1994-10-14 | 1994-10-14 | Verwendung von Guanidiniumsalzen ungesättigter Fettsäuren als Korrosionsschutzwirkstoff |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996012054A1 true WO1996012054A1 (de) | 1996-04-25 |
Family
ID=6530785
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1995/003931 WO1996012054A1 (de) | 1994-10-14 | 1995-10-05 | Verwendung von guanidiniumsalzen ungesättigter fettsäuren als korrosionsschutzwirkstoff |
Country Status (9)
Country | Link |
---|---|
US (1) | US5749947A (de) |
EP (1) | EP0786019B1 (de) |
JP (1) | JPH10507231A (de) |
AT (1) | ATE180022T1 (de) |
CA (1) | CA2202678A1 (de) |
DE (2) | DE4436764A1 (de) |
ES (1) | ES2132722T3 (de) |
FR (1) | FR2725599B3 (de) |
WO (1) | WO1996012054A1 (de) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19747895A1 (de) * | 1997-10-30 | 1999-05-06 | Henkel Kgaa | Metallbehandlungsflüssigkeit für den neutralen pH-Bereich |
FR2795432B1 (fr) * | 1999-06-28 | 2001-08-24 | Atofina | Compositions inhibitrices de la corrosion pour fluides de transfert de chaleur |
DE102007027372A1 (de) * | 2007-06-11 | 2008-12-18 | Cognis Oleochemicals Gmbh | Verfahren zur Hydrierung von Glycerin |
US8766024B2 (en) * | 2009-11-20 | 2014-07-01 | Phillips 66 Company | Process to mitigate the corrosion of oils/fats |
WO2016068336A1 (ja) * | 2014-10-30 | 2016-05-06 | 旭化成ケミカルズ株式会社 | 経皮吸収促進剤及び経皮吸収促進助剤 |
EP3842486A4 (de) * | 2018-08-24 | 2021-07-21 | Mitsubishi Gas Chemical Company, Inc. | Kautschukzusammensetzung und reifen |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2978415A (en) * | 1957-04-17 | 1961-04-04 | American Cyanamid Co | Guanidine soaps as dry cleaning detergents |
DE3203491A1 (de) * | 1982-02-03 | 1983-08-11 | Henkel KGaA, 4000 Düsseldorf | Verwendung von stearinsaeurederivaten als korrosionsschutzmittel |
EP0566956A1 (de) * | 1992-04-22 | 1993-10-27 | Hoechst Aktiengesellschaft | Korrosionsschutzmittel |
DE4237501A1 (de) * | 1992-11-06 | 1994-05-11 | Henkel Kgaa | Dialkylether in Metalloberflächen-Behandlungsmitteln |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3907392A1 (de) * | 1989-03-08 | 1990-09-13 | Henkel Kgaa | Ester von carbonsaeuren mittlerer kettenlaenge als bestnadteil der oelphase in invert-bohrspuelschlaemmen |
DE3907391A1 (de) * | 1989-03-08 | 1990-09-13 | Henkel Kgaa | Verwendung ausgewaehlter esteroele niederer carbonsaeuren in bohrspuelungen |
US5318954A (en) * | 1989-03-08 | 1994-06-07 | Henkel Kommanditgesellschaft Auf Aktien | Use of selected ester oils of low carboxylic acids in drilling fluids |
DE3929069A1 (de) * | 1989-09-01 | 1991-03-07 | Henkel Kgaa | Neues basisoel fuer die schmierstoffindustrie |
DZ1577A1 (fr) * | 1991-05-08 | 2002-02-17 | Hoechst Ag | Emploi d'acetals. |
DE4323771A1 (de) * | 1993-07-15 | 1995-01-19 | Henkel Kgaa | Grundöl auf Triglyceridbasis für Hydrauliköle |
DE4323908A1 (de) * | 1993-07-16 | 1995-01-19 | Henkel Kgaa | Verfahren zur Herstellung von O/W-Emulsionen zum Reinigen und Passivieren von Metalloberflächen |
-
1994
- 1994-10-14 DE DE4436764A patent/DE4436764A1/de not_active Withdrawn
-
1995
- 1995-10-05 AT AT95935435T patent/ATE180022T1/de not_active IP Right Cessation
- 1995-10-05 EP EP95935435A patent/EP0786019B1/de not_active Expired - Lifetime
- 1995-10-05 CA CA002202678A patent/CA2202678A1/en not_active Abandoned
- 1995-10-05 JP JP8512901A patent/JPH10507231A/ja active Pending
- 1995-10-05 FR FR9511700A patent/FR2725599B3/fr not_active Expired - Fee Related
- 1995-10-05 ES ES95935435T patent/ES2132722T3/es not_active Expired - Lifetime
- 1995-10-05 DE DE59505930T patent/DE59505930D1/de not_active Expired - Fee Related
- 1995-10-05 WO PCT/EP1995/003931 patent/WO1996012054A1/de active IP Right Grant
- 1995-10-05 US US08/817,458 patent/US5749947A/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2978415A (en) * | 1957-04-17 | 1961-04-04 | American Cyanamid Co | Guanidine soaps as dry cleaning detergents |
DE3203491A1 (de) * | 1982-02-03 | 1983-08-11 | Henkel KGaA, 4000 Düsseldorf | Verwendung von stearinsaeurederivaten als korrosionsschutzmittel |
EP0566956A1 (de) * | 1992-04-22 | 1993-10-27 | Hoechst Aktiengesellschaft | Korrosionsschutzmittel |
DE4237501A1 (de) * | 1992-11-06 | 1994-05-11 | Henkel Kgaa | Dialkylether in Metalloberflächen-Behandlungsmitteln |
Non-Patent Citations (2)
Title |
---|
CHEMICAL ABSTRACTS, vol. 115, no. 12, 23 September 1991, Columbus, Ohio, US; abstract no. 118225y, HORI T.: "Corrosion prevention by guanidine salts" * |
HORI T., BOSEI KANRI, vol. 35, no. 4, 1 April 1991 (1991-04-01), JP, pages 131 - 147 * |
Also Published As
Publication number | Publication date |
---|---|
US5749947A (en) | 1998-05-12 |
ES2132722T3 (es) | 1999-08-16 |
EP0786019A1 (de) | 1997-07-30 |
JPH10507231A (ja) | 1998-07-14 |
DE59505930D1 (de) | 1999-06-17 |
DE4436764A1 (de) | 1996-04-18 |
EP0786019B1 (de) | 1999-05-12 |
FR2725599B3 (fr) | 1999-08-06 |
ATE180022T1 (de) | 1999-05-15 |
CA2202678A1 (en) | 1996-04-25 |
FR2725599A1 (fr) | 1996-04-19 |
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