US2734807A - Biguanide derivatives as corrosion - Google Patents
Biguanide derivatives as corrosion Download PDFInfo
- Publication number
- US2734807A US2734807A US2734807DA US2734807A US 2734807 A US2734807 A US 2734807A US 2734807D A US2734807D A US 2734807DA US 2734807 A US2734807 A US 2734807A
- Authority
- US
- United States
- Prior art keywords
- water
- corrosion
- substituted
- biguanide
- rust
- 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.)
- Expired - Lifetime
Links
- 238000005260 corrosion Methods 0.000 title claims description 114
- 150000004283 biguanides Chemical class 0.000 title claims description 72
- 229910001868 water Inorganic materials 0.000 claims description 144
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 142
- 230000002401 inhibitory effect Effects 0.000 claims description 80
- 239000003921 oil Substances 0.000 claims description 76
- 229910052751 metal Inorganic materials 0.000 claims description 62
- 239000002184 metal Substances 0.000 claims description 62
- 150000002430 hydrocarbons Chemical class 0.000 claims description 34
- 239000004215 Carbon black (E152) Substances 0.000 claims description 30
- 238000004642 transportation engineering Methods 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N CTK2H8874 Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000011368 organic material Substances 0.000 description 82
- 239000003112 inhibitor Substances 0.000 description 62
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 36
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 32
- -1 greases Substances 0.000 description 30
- 125000001183 hydrocarbyl group Chemical group 0.000 description 28
- 239000000203 mixture Substances 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 20
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 20
- 239000000295 fuel oil Substances 0.000 description 16
- 229910052742 iron Inorganic materials 0.000 description 16
- 125000004432 carbon atoms Chemical group C* 0.000 description 14
- 231100000078 corrosive Toxicity 0.000 description 14
- 231100001010 corrosive Toxicity 0.000 description 14
- 239000003502 gasoline Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 150000002829 nitrogen Chemical group 0.000 description 14
- 230000003405 preventing Effects 0.000 description 14
- 239000000654 additive Substances 0.000 description 12
- 229940058933 biguanide antimalarials Drugs 0.000 description 12
- 229940090145 biguanide blood glucose lower drugs Drugs 0.000 description 12
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N diguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 12
- HWEQLUZIUMZTIC-UHFFFAOYSA-N 2-decyl-1-(diaminomethylidene)guanidine Chemical compound CCCCCCCCCCN=C(N)N=C(N)N HWEQLUZIUMZTIC-UHFFFAOYSA-N 0.000 description 10
- 230000000996 additive Effects 0.000 description 10
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecan-1-amine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 10
- YXPRMRXFPJPEAD-UHFFFAOYSA-N C1(=CC=CC=C1)N(C(=N)NC(=N)N)CCCCCCC Chemical compound C1(=CC=CC=C1)N(C(=N)NC(=N)N)CCCCCCC YXPRMRXFPJPEAD-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- CUQCMXFWIMOWRP-UHFFFAOYSA-N phenyl biguanide Chemical compound NC(N)=NC(N)=NC1=CC=CC=C1 CUQCMXFWIMOWRP-UHFFFAOYSA-N 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- PSOOCNCKIQJEPF-UHFFFAOYSA-N C(CCCCCCCCCCCCCC)NC(=N)NC(=N)N Chemical compound C(CCCCCCCCCCCCCC)NC(=N)NC(=N)N PSOOCNCKIQJEPF-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002485 combustion reaction Methods 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 description 6
- 239000012169 petroleum derived wax Substances 0.000 description 6
- 235000019381 petroleum wax Nutrition 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- DRFIDKXKHBUJDB-UHFFFAOYSA-N 1,1-dibutyl-3-(diaminomethylidene)guanidine Chemical compound CCCCN(CCCC)C(=N)N=C(N)N DRFIDKXKHBUJDB-UHFFFAOYSA-N 0.000 description 4
- RMQOXNXLVICLNK-UHFFFAOYSA-N 1,4-dihydro-1,3,5-triazine Chemical class C1NC=NC=N1 RMQOXNXLVICLNK-UHFFFAOYSA-N 0.000 description 4
- KOUTYMWBZYMGBR-UHFFFAOYSA-N 1-(diaminomethylidene)-2-dodecylguanidine Chemical compound CCCCCCCCCCCCN=C(N)N=C(N)N KOUTYMWBZYMGBR-UHFFFAOYSA-N 0.000 description 4
- SPZSHRCACHVFJR-UHFFFAOYSA-N 1-(diaminomethylidene)-2-heptylguanidine Chemical compound CCCCCCCN=C(N)N=C(N)N SPZSHRCACHVFJR-UHFFFAOYSA-N 0.000 description 4
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Chemical compound CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 description 4
- JTPHTWMZPJTOSI-UHFFFAOYSA-N 1-(diaminomethylidene)-2-nonylguanidine Chemical compound CCCCCCCCCN=C(N)N=C(N)N JTPHTWMZPJTOSI-UHFFFAOYSA-N 0.000 description 4
- MNWJUMZPXYLPGT-UHFFFAOYSA-N 1-(diaminomethylidene)-2-octadecylguanidine Chemical compound CCCCCCCCCCCCCCCCCCN=C(N)N=C(N)N MNWJUMZPXYLPGT-UHFFFAOYSA-N 0.000 description 4
- ASLUEXWHMHPYQQ-UHFFFAOYSA-N 3-(diaminomethylidene)-1,1-dipentylguanidine Chemical compound CCCCCN(C(=N)N=C(N)N)CCCCC ASLUEXWHMHPYQQ-UHFFFAOYSA-N 0.000 description 4
- YCSQZLPVAFDPDM-UHFFFAOYSA-N 3-(diaminomethylidene)-1,1-diphenylguanidine Chemical compound C=1C=CC=CC=1N(C(=N)N=C(N)N)C1=CC=CC=C1 YCSQZLPVAFDPDM-UHFFFAOYSA-N 0.000 description 4
- XXDXKMDNFSOVHZ-UHFFFAOYSA-N C(CCCCCCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 Chemical compound C(CCCCCCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 XXDXKMDNFSOVHZ-UHFFFAOYSA-N 0.000 description 4
- ORXFEVODXBNROV-UHFFFAOYSA-N C(CCCCCCCCCCCCCCC)NC(=N)NC(=N)N Chemical compound C(CCCCCCCCCCCCCCC)NC(=N)NC(=N)N ORXFEVODXBNROV-UHFFFAOYSA-N 0.000 description 4
- 210000003491 Skin Anatomy 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000010687 lubricating oil Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000003884 phenylalkyl group Chemical group 0.000 description 4
- 238000005554 pickling Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (Z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
- WSRHQODSPFXZSV-UHFFFAOYSA-N 1,1-dibutyl-3-(diaminomethylidene)-2-ethylguanidine Chemical compound CCCCN(CCCC)C(=NCC)N=C(N)N WSRHQODSPFXZSV-UHFFFAOYSA-N 0.000 description 2
- FZGQFJNMPUUPOY-UHFFFAOYSA-N 1,1-dicyclohexyl-3-(diaminomethylidene)guanidine Chemical class C1CCCCC1N(C(=N)N=C(N)N)C1CCCCC1 FZGQFJNMPUUPOY-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-Triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- QXBVNDNLFDDQSX-UHFFFAOYSA-N 1,4-dihydro-1,3,5-triazine-2,6-diamine Chemical class NC1=NC(N)=NCN1 QXBVNDNLFDDQSX-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QPUAWEXLLDSJBV-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2,3-dimethylphenyl)guanidine Chemical compound CC1=CC=CC(N=C(N)N=C(N)N)=C1C QPUAWEXLLDSJBV-UHFFFAOYSA-N 0.000 description 2
- SQZCAOHYQSOZCE-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N=C(N)N=C(N)N SQZCAOHYQSOZCE-UHFFFAOYSA-N 0.000 description 2
- UUBZPMKBMHXGNE-UHFFFAOYSA-N 1-(diaminomethylidene)-2-naphthalen-1-ylguanidine Chemical compound C1=CC=C2C(N=C(N)N=C(N)N)=CC=CC2=C1 UUBZPMKBMHXGNE-UHFFFAOYSA-N 0.000 description 2
- GGVQUXMNYQSGIN-UHFFFAOYSA-N 1-(diaminomethylidene)-2-octylguanidine Chemical compound CCCCCCCCN=C(N)N=C(N)N GGVQUXMNYQSGIN-UHFFFAOYSA-N 0.000 description 2
- ZJDKLQSQLISLOI-UHFFFAOYSA-N 1-(diaminomethylidene)-2-tetradecylguanidine Chemical compound CCCCCCCCCCCCCCN=C(N)N=C(N)N ZJDKLQSQLISLOI-UHFFFAOYSA-N 0.000 description 2
- DAWJEWKAWPLECA-UHFFFAOYSA-N 1-(diaminomethylidene)-2-undecylguanidine Chemical compound CCCCCCCCCCCN=C(N)N=C(N)N DAWJEWKAWPLECA-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 1-butanal Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- KDHDQYJTIJDMMZ-UHFFFAOYSA-N 1-butyl-3-(diaminomethylidene)-1-ethylguanidine Chemical compound CCCCN(CC)C(=N)N=C(N)N KDHDQYJTIJDMMZ-UHFFFAOYSA-N 0.000 description 2
- YLJAYDGLQIFDND-UHFFFAOYSA-N 1-butyl-3-(diaminomethylidene)-1-phenylguanidine Chemical compound CCCCN(C(=N)NC(N)=N)C1=CC=CC=C1 YLJAYDGLQIFDND-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical class CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- BDPICBCRPFYBKJ-UHFFFAOYSA-N 2-propyl-1-(N'-propylcarbamimidoyl)guanidine Chemical compound CCCN=C(N)NC(N)=NCCC BDPICBCRPFYBKJ-UHFFFAOYSA-N 0.000 description 2
- WEWNALWBQHKZPY-UHFFFAOYSA-N 3-(diaminomethylidene)-1,1,2-triethylguanidine Chemical compound CCN=C(NC(N)=N)N(CC)CC WEWNALWBQHKZPY-UHFFFAOYSA-N 0.000 description 2
- WUPJOJRPQKSKDY-UHFFFAOYSA-N 3-(diaminomethylidene)-1,1-diethyl-2-propylguanidine Chemical compound CCCN=C(N=C(N)N)N(CC)CC WUPJOJRPQKSKDY-UHFFFAOYSA-N 0.000 description 2
- SQTHMGUHVUGMOU-UHFFFAOYSA-N 3-(diaminomethylidene)-1,1-dipropylguanidine Chemical compound CCCN(CCC)C(=N)NC(N)=N SQTHMGUHVUGMOU-UHFFFAOYSA-N 0.000 description 2
- KZZXOYFLVCIWCW-UHFFFAOYSA-N 3-(diaminomethylidene)-1-ethyl-1-phenylguanidine Chemical compound NC(N)=NC(=N)N(CC)C1=CC=CC=C1 KZZXOYFLVCIWCW-UHFFFAOYSA-N 0.000 description 2
- WFYPAYHESAQPHA-UHFFFAOYSA-N 3-(diaminomethylidene)-1-methyl-1-pentylguanidine Chemical compound CCCCCN(C)C(=N)N=C(N)N WFYPAYHESAQPHA-UHFFFAOYSA-N 0.000 description 2
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- VPXUMOYYEKCKIL-UHFFFAOYSA-N C(CCCC)N(C(=N)NC(=N)N)CCCCCCCCCCCC Chemical compound C(CCCC)N(C(=N)NC(=N)N)CCCCCCCCCCCC VPXUMOYYEKCKIL-UHFFFAOYSA-N 0.000 description 2
- RCRILPUBKJNHIV-UHFFFAOYSA-N C(CCCC)N(C(=N)NC(=N)N)CCCCCCCCCCCCC Chemical compound C(CCCC)N(C(=N)NC(=N)N)CCCCCCCCCCCCC RCRILPUBKJNHIV-UHFFFAOYSA-N 0.000 description 2
- QSGPTXVGZXWYLQ-UHFFFAOYSA-N C(CCCC)N(C(=N)NC(=N)N)CCCCCCCCCCCCCC Chemical compound C(CCCC)N(C(=N)NC(=N)N)CCCCCCCCCCCCCC QSGPTXVGZXWYLQ-UHFFFAOYSA-N 0.000 description 2
- BCRVBEVRJCMDRX-UHFFFAOYSA-N C(CCCC)N(C(=N)NC(=N)N)CCCCCCCCCCCCCCC Chemical compound C(CCCC)N(C(=N)NC(=N)N)CCCCCCCCCCCCCCC BCRVBEVRJCMDRX-UHFFFAOYSA-N 0.000 description 2
- YOQDZUKBPJQNJJ-UHFFFAOYSA-N C(CCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 Chemical compound C(CCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 YOQDZUKBPJQNJJ-UHFFFAOYSA-N 0.000 description 2
- ITONUSFGXJDGQR-UHFFFAOYSA-N C(CCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 Chemical compound C(CCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 ITONUSFGXJDGQR-UHFFFAOYSA-N 0.000 description 2
- NXPQEQKUILQZCT-UHFFFAOYSA-N C(CCCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC2=CC=CC=C12 Chemical compound C(CCCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC2=CC=CC=C12 NXPQEQKUILQZCT-UHFFFAOYSA-N 0.000 description 2
- CNGBKUCQBROJKU-UHFFFAOYSA-N C(CCCCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 Chemical compound C(CCCCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 CNGBKUCQBROJKU-UHFFFAOYSA-N 0.000 description 2
- GHXQTZHGKMEDND-UHFFFAOYSA-N C(CCCCCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 Chemical compound C(CCCCCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 GHXQTZHGKMEDND-UHFFFAOYSA-N 0.000 description 2
- RCSYLDCIDRTRCH-UHFFFAOYSA-N C(CCCCCCCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 Chemical compound C(CCCCCCCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 RCSYLDCIDRTRCH-UHFFFAOYSA-N 0.000 description 2
- VYYWRIZIEBWOEZ-UHFFFAOYSA-N C(CCCCCCCCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 Chemical compound C(CCCCCCCCCCCCC)N(C(=N)NC(=N)N)C1=CC=CC=C1 VYYWRIZIEBWOEZ-UHFFFAOYSA-N 0.000 description 2
- ZATSMOCOJIPPRD-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCC)NC(=N)NC(=N)N Chemical compound C(CCCCCCCCCCCCCCCC)NC(=N)NC(=N)N ZATSMOCOJIPPRD-UHFFFAOYSA-N 0.000 description 2
- JUEUXYWCNAAAAZ-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCCC)NC(=N)NC(=N)N Chemical compound C(CCCCCCCCCCCCCCCCCC)NC(=N)NC(=N)N JUEUXYWCNAAAAZ-UHFFFAOYSA-N 0.000 description 2
- YSYRYEIQIGWMTH-UHFFFAOYSA-N C1(CCCCC1)N(C(=N)NC(=N)N)C1=CC=CC=C1 Chemical class C1(CCCCC1)N(C(=N)NC(=N)N)C1=CC=CC=C1 YSYRYEIQIGWMTH-UHFFFAOYSA-N 0.000 description 2
- WWXJAWIJSDLMOI-UHFFFAOYSA-N C1(CCCCC1)N(C(NC(N(C1CCCCC1)C1CCCCC1)=N)=N)C1CCCCC1 Chemical compound C1(CCCCC1)N(C(NC(N(C1CCCCC1)C1CCCCC1)=N)=N)C1CCCCC1 WWXJAWIJSDLMOI-UHFFFAOYSA-N 0.000 description 2
- JQVWKEVVZGLZJM-UHFFFAOYSA-N CN(C(=N)NC(=N)N)CCCCCCC Chemical compound CN(C(=N)NC(=N)N)CCCCCCC JQVWKEVVZGLZJM-UHFFFAOYSA-N 0.000 description 2
- FUEWFBBOYHGPEJ-UHFFFAOYSA-N CN(C(=N)NC(=N)N)CCCCCCCC Chemical compound CN(C(=N)NC(=N)N)CCCCCCCC FUEWFBBOYHGPEJ-UHFFFAOYSA-N 0.000 description 2
- SZGUVHMNCZKUMB-UHFFFAOYSA-N CN(C(=N)NC(=N)N)CCCCCCCCC Chemical compound CN(C(=N)NC(=N)N)CCCCCCCCC SZGUVHMNCZKUMB-UHFFFAOYSA-N 0.000 description 2
- JEZUKOZJIGKDSO-UHFFFAOYSA-N CN(C(=N)NC(=N)N)CCCCCCCCCCCCCCCC Chemical compound CN(C(=N)NC(=N)N)CCCCCCCCCCCCCCCC JEZUKOZJIGKDSO-UHFFFAOYSA-N 0.000 description 2
- KAUUNQYAAUMVCD-UHFFFAOYSA-N CN(C(=N)NC(=N)N)CCCCCCCCCCCCCCCCC Chemical compound CN(C(=N)NC(=N)N)CCCCCCCCCCCCCCCCC KAUUNQYAAUMVCD-UHFFFAOYSA-N 0.000 description 2
- UEKFQRHCYOFICL-UHFFFAOYSA-N CN(C(=N)NC(=N)N)CCCCCCCCCCCCCCCCCCC Chemical compound CN(C(=N)NC(=N)N)CCCCCCCCCCCCCCCCCCC UEKFQRHCYOFICL-UHFFFAOYSA-N 0.000 description 2
- 229910000975 Carbon steel Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L Copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 229910000881 Cu alloy Inorganic materials 0.000 description 2
- IZEKFCXSFNUWAM-UHFFFAOYSA-N Dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N Methyl vinyl ketone Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- FXZWPZMCZNJILD-UHFFFAOYSA-N N-[(6-bromopyridin-3-yl)methyl]ethanamine;hydrochloride Chemical compound Cl.CCNCC1=CC=C(Br)N=C1 FXZWPZMCZNJILD-UHFFFAOYSA-N 0.000 description 2
- 239000004264 Petrolatum Substances 0.000 description 2
- 229940066842 Petrolatum Drugs 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 238000005296 abrasive Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000001464 adherent Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000010962 carbon steel Substances 0.000 description 2
- 238000002144 chemical decomposition reaction Methods 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- 239000007799 cork Substances 0.000 description 2
- 238000005536 corrosion prevention Methods 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N cyanoguanidine Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- WJYIASZWHGOTOU-UHFFFAOYSA-N heptan-1-amine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 230000001050 lubricating Effects 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 230000003389 potentiating Effects 0.000 description 2
- 230000003449 preventive Effects 0.000 description 2
- 239000002987 primer (paints) Substances 0.000 description 2
- 230000001737 promoting Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective Effects 0.000 description 2
- 230000002829 reduced Effects 0.000 description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- IXBPPZBJIFNGJJ-UHFFFAOYSA-N sodium;cyanoiminomethylideneazanide Chemical compound [Na+].N#C[N-]C#N IXBPPZBJIFNGJJ-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
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
- C23F11/146—Nitrogen-containing compounds containing a multiple nitrogen-to-carbon bond
-
- 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
- C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom
Definitions
- various water soluble corrosion inhibitors may be utilized for preventing corrosion of gasoline or fuel oil storage tanks by water collecting in the bottom of the tank, a suitable and sutficient quantity of the desired inhibitor being injected in the bottom of the tank -to inhibit both water already separated or intentionally maintained therein, and water which may later separate from the gasoline or fuel oil and collect in the bottom of the tank.
- part of the water which separates collects on the tank wall, corroding and damaging the same, the corrosion products in turn contaminating the gasoline or fuel oil.
- Analogous corrosion problems occur in numerous other fields; for example, in the lubrication of internal combustion engines or steam engines including turbines, and other similar machinery, quantities of water are often as a result of the condensation of water from the atmosphere, or in the case of internal combustion engines as a result of dispersion or absorption in lubricating oil or water formed as a product of fuel compositions. Water, in such instances, corrodes the various metal parts of the machinery with which it comes in contact, the corrosion products causing further mechanical damages to bearing surfaces and the like due to their abrasive nature and catalytically promoting the chemical degradation of the lubricant.
- the inhibitors known to the art have not always been entirely satisfactory, the organic material soluble inhibitors being, in general, relatively inefiective water corrosion inhibitors, and the water soluble inhibitors being difficult and in most instances impractical in their application.
- the same or similar problems arise in the preparation and use of various coating compositions such as greases, glass, household oils, paints, lacquers, Water soluble paints, etc., which are often applied to metal surfaces for protective or other purposes.
- a further object is to provide inhibitors of this type which will satisfactorily prevent corrosion of certain metal surfaces by water in contact with said organic materials and said'metal surfaces.
- Further objects are to provide water corrosion inhibitors which are stable at ordinary temperatures of use, easily and inexpensively prepared and which will not deleteriously affect organic materials with which they are incorporated.
- the present invention relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material containing dissolved therein in minor proportion, but in amount sufiicient to inhibit corrosion of metal surfaces by said water, of a biguanide derivative.
- the present invention relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material having dissolved therein in minor proportion, but in amount suificient to inhibit corrosion of metal surfaces by said water, N-substituted biguanide.
- the present invention relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material having dissolved therein in minor proportion, but in amount suflicient to inhibit corrosion of metal surfaces by said water, a N ,N -di-substituted biguanide.
- the present invention relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material having dissolved therein in minor proportion, but in amount suificient to inhibit corrosion of metal surfaces by said water, N -dodecylbiguam'de.
- the present invention relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material having dissolved therein in minor proportion, but in amount sufficient to inhibit corrosion of metal surfaces by said water, N -phenyl-N -heptylbiguanide.
- the present invention in another specific embodiment relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material having dissolved therein in minor proportion, but in an amount sufficient to inhibit corrosion of metal surfaces by said water, a 2,6-diamino-1,4-dihydro-l,3,5-triazine.
- the present invention relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material having dissolved therein in minor proportion, but in amount sufficient to inhibit corrosion of metal surfaces by said water, 2-amino-6-dodccylphenylamino-1,4-dihydro- 1,3,5-triazine.
- certain biguanide derivatives are excellent water corrosion inhibitors and are soluble in organic materials, thereby preventing corrosion of metal surfaces in contact with said organic material andwater. It has been found further that these biguanide derivatives, although probably soluble only in the organic material, prevent corrosion of the metal surfaces in contact with the water only, said water being in contact with said organic material.
- R is selected from the groups consisting of hydrocarbon and substituted hydrocarbon groups, and where R1, R2, and R3 are selected from the group consisting of hydrogen, hydrocarbon and substituted hydrocarbon groups.
- the substituted biguanides are numbered as follows: Beginning with one of the terminal nitrogen atoms, in our case conveniently being the nitrogen atom at the left of the general structure, and numbering this nitrogen as 1, the remaining nitrogen atoms are numbered, reading from left to right, 2, 3, 4, and 5.
- certain biguanide derivatives of the present invention require that one terminal nitrogen atom, number 1, be substituted by at least 1 hydrocarbon or substituted hydrocarbon group.
- further substitution of the terminal nitrogen atoms may take place and this substitution may be such that both terminal nitrogen atoms, numbers 1 and 5, are each substituted by at least 1 hydrocarbon or substituted hydrocarbon group and may be completely substituted by hydrocarbon or substituted hydrocarbon groups.
- This particular substitution is an essential feature of the present invention because it results, not only in a corrosion inhibitor which etfectively retards corrosion of metal surfaces in contact with an organic material and water, but also in a compound which is readily soluble in said organic material, and therefore, may be readily incorporated therein.
- the readily solubility of the corrosion inhibitor in the organic material serves the function of providing a corrosion inhibitor which is effective in preventing corrosion of metal surfaces in contact both wit-h an organic material and with water in contact with said organic material.
- any suitable substituted biguanide may be used in accordance with the present invention. It generally is preferred that the additive compound contains at least 6 carbon atoms, although in some cases additives containing a fewer number of carbon atoms may be. used.
- N -substituted biguan'idcs containing 6. or more carbon atoms include N -hexylbiguanide, N -heptylbiguanide,
- 1,5-substituted biguanides containing 6 or more carbon atoms include N -methyl-N -amylbiguanide, N -rnethyl-N -hexylbiguanide, N methyl-N -heptylbiguanide, N -methyl-N -octylbiguanide, N -methyl-N -nonylbiguanide, N -methyl-N decylbiguanide, N methyl N5 undecylbiguanide, N methyl-N -dodecylbiguanidc, N -methyl-N -tridecylbiguanide, N -methyl-N -tetradecylbiguanide, N -methyl-N pentadecylbiguanide, N -methyl-N -hexadecylbiguanide
- biguanides include N ,N -diphenylbiguanide, N -alkylphenyl- N -phenylbiguanide, N -alkylphenyl-N -alkylphenylbiguanides, N -phenylalkyl-N -phenylbiguanides, N -phenyl- 'nide, N ,N ,N ,N -tetracyclohexylalkylbiguanide, etc.
- Trialkylbiguanides include those in which the N nitrogen atom is di-substituted and the N nitrogen atom is mono-substituted with hydrocarbon groups as hereinbe fore set forth.
- Typical compounds in this class include N ,N ,N triethylbiguanide, N propyl-N ,N -diethylbiguanide, N -butyl-N ,N -diethylbiguanide, etc., N -methyl- N ,N -dipropylbiguanide, N -ethyl-N ,N -d1propylb guanide, N N ,N -tripropylbiguanide, N -butyl-N ,N -d1propylbiguanide, etc., N -n1ethyl-N ,N -dibutylbiguanide, N ethyl-N ,N -dibutyl
- N ,N ,N ,N -tetra-substituted-biguanides are within the scope of the present invention and the substituent groups may comprise alkyl, phenyl-phenylalkyl, alkylphenyl, cyclohexyl, alkylcyclohexyl, and cyclohexylalkyl groups.
- Particularly preferred compounds include those in which the substituent group is the same because this simplifies manufacture of the compounds and thus include N ,N N ,N -tetraethylbiguanide, N ,N ,N ,N -tetrapropylbiguanide, N ,N ,N ,N -tetrabutylbiguanide, N ,N ,N ,N -tetraamylbiguanide, N ,N ,N ,N -tetrahexylbiguanide, N ,N N ,N -tetraheptylbiguanide, etc., N ,N ,N ,N -tetraphenylbiguanide, N ,N ,N ,N -tetraalkylphenylbiguanide, N ,N N ,N -tetraphenylalkylbiguanide, N ,N ,N tetracyclo
- N -phenyl-N -heptylbiguanide may be prepared by commingling the desired aryl-diazonium halide with dicyandiamide and decompoing the resultant product to aryl-dicyandiamide, which is reacted with primary heptyl amine in the presence of copper sulfate.
- a tri-substituted biguanide is desired, a secondary amine is employed.
- the tetrasubstituted biguanides may be prepared by the reaction of two molecular proportions of the desired amine hydrochloride with sodium dicyanamide.
- R may be selected from hydrocarbon and substituted hydrocarbon groups
- R1, R2 and R3 may be selected from the hydrogen, hydrocarbon and substituted hydrocarbon groups
- R4 may be selected from hydrogen, hydrocarbon and substituted hydrocarbon groups.
- Compounds of this structure include 2-arnino-6-dodecylphenylamino-l,4-dihydro-1,3,5-triazine, 2-amino-4-phenyl- 6 dodecylphenylamino 1,4 dihydro 1,3,5 triazine, 2- amino 4 n propyl-6-dodecylphenylamino-1,4-dihydro- 1,3,5-triazine, Z-amino-4-isopropyl-6-dodecylphenylamino- 1,4 dihydro 1,3,5 triazine, 2-amino-4-butyl-6-dodecylphenylamino-1,4-dihydro-1,3,5-triazine, 2-
- 1,4-dihydro-1,3,5-triazines may be prepared by the reaction of biguanides with aldehydes.
- the biguanide is suitably substituted.
- dodecylphenylbiguanide is reacted with butyraldehyde, the reaction being efiected by merely boiling equimolecular quantities of the components or solutions thereof, with constant water separation.
- the corrosion inhibitors of the present invention may comprise the specific compounds named above alone or in admixture with various isomers thereof. Furthermore, it is understood that the various corrosion inhibitors which may be utilized in accordance with the present invention are not necessarily equivalent for use in the inhibition of difierent organic compounds which may be treated in accordance with the present invention. Furthermore, it is understood that the particular additive to be used should be selected so as to meet the specific requirements of the particular material being stabilized. For example, in the treatment of fuel oil, the R group should be selected so that the additive contains a total of from about 6 to about 30 carbon atoms permole in order that the additive may not be too volatile, will be readily soluble, etc. It is appreciated that the particular selection of the substituent groups will depend upon the particular organic material in which the additive is to be employed.
- the presently described inhibitors are most effective in preventing water corrosion of ferrous metals, aluminum, nickel, chromium, and alloys of these metals. To a lesser extent, the biguanide derivative inhibitors are also beneficial in preventing Water corrosion of copper and copper alloys.
- the inhibitors of the present invention may be incorporated into any organic material, whether solid, semisolid or liquid in which they are soluble and with which Thus they may be added to hydrocarbons (which may be paraffinic, olefinic, naphthenic, or aromatic) of the type described, or to chlorinated hydrocarbons, alcohols, esters, ethers, ketones, nitriles, amino compounds, amides, fats and fatty oils (edible and non-edible) paints, varnishes, natural waxes, oils, etc.
- hydrocarbons which may be paraffinic, olefinic, naphthenic, or aromatic
- chlorinated hydrocarbons alcohols, esters, ethers, ketones, nitriles, amino compounds, amides, fats and fatty oils (edible and non-edible) paints, varnishes, natural waxes, oils, etc.
- 0.0001 to 0.5% by weight of the biguanide derivative will generally be found satisfactory for inhibition of water corrosion, although lower or higher amounts may be used.
- the precise amount of inhibitor to be utilized in each instance will, of course, vary with the particular conditions at hand and should be determined experimentally, particularly when usually severe corrosion conditions are to be overcome. However, in the majority of practical applications when handling substantially water insoluble organic materials of this type, the addition of approximately 0.001 to about 0.1% by weight of the inhibitor will be found satisfactory.
- inhibitors up to about 2.0% by weight may be required for inhibiting other organic materials, particularly those miscible with water, such as alcohols, ketones and the like, as for example, methyl alcohol, ethyl alcohol, propyl alcohol, acetone, methyl ethyl ketones, methyl vinyl ketone, dioxane, etc.
- Oil base coatings 0.01% to 1% by weight
- wax base coatings other petroleum wax (petrolatum) base coatings
- petroleum wax base coatings 0.01% to 5% by weight or higher based on the petroleum wax contained in the particular coating
- a primer coating for paint 0.01% to 1.0% by weight based on the dry constituents
- lubricant compositions such as lubricating oils for internal combustion engines, turbines and the like, greases, semi-greases, etc., 0.001% to about 1.0% by weight
- general purpose oils such as household oils, 0.01% to 1.0%.
- the following specific examples serve to illustrate the effectiveness of the presently disclosed corrosion inhibitors.
- the procedure used in each of the following examples is given as follows: The samples were stored in clear 4 ounce bottles in a 100 F. constant temperature room in the absence of light. To make up a sample, 50 grams of an oil was placed in the bottle, together with 5 ml. of distilled water or synthetic sea water. By weight, 0.01% of the corrosion inhibitor was added to the oil; the corrosion inhibitor had previously been dissolved in benzene or isopropyl alcohol in a ratio of 0.0050 grams per milliliter of solvent, and thereby the oil could accurately be inhibited by using 1 ml. of the solvent solution from a pipette. An iron strip was then added, the bottle corked and thoroughly shaken.
- Armeen 12D is a commercially available mixture of alkyl amines, predominately On, which has been purified by fractionation; the water layer under the oil in this case was b
- Armeen C is a commercially available mixture of alkyl amines, predominately C12.
- Example II Virgin Oil with Distilled H10 v Rust on Rust Rust on Rust Rust on Rust az gg by Strip in Loose m Strip in Loose in Strip in Loose m 8 Oil Level 11.0 on Level Hlo Oil Level mo After 2 days After 5 days After 30 days 1. Blank... slight... medium. medium. medium. 2.
- Armeen C biguanide do.. .-.do
- N -phenylbiguanide do..--- slight.-.. negative. slight.--. negati negative 5.
- Example 111 Cracked Oil with Synthetic Sea H10 Rust on Rust Rust on Rust Rust on Rust 00170310 i i 001% by Strip in Loose in Strip in Loose in Strip in Loose in We g Oil Level Hoo Oil Level 11,0 on Level mo After 2 days After 5 days After days 1. Blank heavy..- heavy... heavy--- heavy. 2. Armeen 12D biguanl trace-... traee---. trace-... slight. 3. Armeen C biguanide..-.. sligbt.... ...do..-.. slight.... Do. 4. N -phenyl-N -n-heptylbiguanida --do..-.. slight-.. medium. medium. 5. 2-amino-6-dodecylphenylaminomedium. medium. ...do....- Do.
- Example IV Virgin Oil with Synthetic Sea Water Rust on Rust Rust on Rust Rust on Rust corrosion gg by Strip in Loose in Strip in Loose in Strip in Loose in we 011 Level H on Level rrlo Oil Level Hlo After 2 days After 5 days After 30 days 1. Blank heavy-.- heavy... heavy... heavy. 2. Armeen 12D biguani slight.... slight.... slight... medium. 3. Armeen O biguanide- .do....- ---do slight. 4. N -phenylbiguanide traco--.. trace-... Do. 5. N --pl1enyl--N -n-heptylbiguanide. slight.--. slight.. medium.
- the method of inhibiting corrosion of the metal surfaces by said water which comprises dissolving in the organic material from about 0.0001% to about 2% by weight of asubstituted biguanide having a hydrocarbon substituent on at least one of its terminal nitrogen atoms, said organic material and said substituted biguanide being mutually soluble and non-reactive.
- the method of inhibiting corrosion of the metal surfaces by said water which comprises dissolving in the organic material from about 0.0001% to about 2% by weight of a substituted biguanide having a hydrocarbon substituent on each of its terminal nitrogen atoms, said organic material and said substituted biguanide being mutually soluble and non-reactive.
- the method of inhibiting corrosion of the metal surfaces by said water which comprises dissolving in the hydrocarbon oil from about 0.0001% to about 2% by weight of a substituted biguanide having a hydrocarbon substituent on at least one of its terminal nitrogen atoms.
- the method of inhibiting corrosion of the metal surfaces by said water which comprises dissolving in the hydrocarbon oil from about 0.0001% to about 2% by weight of a substituted biguanide having a hydrocarbon substituent on each of its terminal nitrogen atoms.
Description
United States BIGUANIDE DERIVATIVES AS CORROSION ITORS Joseph A. Chenicek, Bensenville, and Ralph B. Thompson,
Hinsdale, Ill., assignors to Universal Oil Products Company, Chicago, 111., a corporation of Delaware No Drawing. Application February 1, 1952, Serial No. 269,614
11 Claims. (Cl. 44-72) to water corrosion prevention 'ice , observed as a separate phase within the lubricating system larly hydrocarbons and similar organic liquid composi- 1 tions, it is often necessary to transport and/or store such materials in metal containers, as in steel or other metal pipe lines, drums, tanks, and the like. Since these materials often contain varying amounts of water in solution or in suspension which may separate, due to temperature changes, internal corrosion of the container by separating water almost invariably occurs to a greater or lesser degree. This problem is especially serious when gasoline or fuel oils are under consideration. In spite of all reasonable and practical precautions during the manufacture of gasoline or fuel oils, when the same are transported in pipe lines or stored in drums or tanks for a period of time, an appreciable quantity of water separation is found as a film or in minute droplets in the pipe line or on container walls or even in small pools in the bottom of the container. This brings about ideal conditions for corrosion and consequent damage to the metal surfaces of the container as well as the even more serious contamination of the gasoline or fuel oil or other material contained therein by the corrosion products.
As a result of the above described corrosion, it has become necessary for manufacturers and shippers of such products to apply various internal coatings to the container walls or to add corrosion inhibitors of one type or another to the product being stored or shipped. It has long been recognized, however, that one of the great difficulties in inhibiting this type of corrosion lies in the fact that those inhibitors which are soluble in organic materials are relatively ineffective in preventing water corrosion of metal surfaces. On the other hand, those inhibitors which are advantageous in preventing this type of corrosion are but slightly, if at all soluble in organic materials and their application is rendered quite difficult for these purposes.
For example, various water soluble corrosion inhibitors may be utilized for preventing corrosion of gasoline or fuel oil storage tanks by water collecting in the bottom of the tank, a suitable and sutficient quantity of the desired inhibitor being injected in the bottom of the tank -to inhibit both water already separated or intentionally maintained therein, and water which may later separate from the gasoline or fuel oil and collect in the bottom of the tank. However, part of the water which separates collects on the tank wall, corroding and damaging the same, the corrosion products in turn contaminating the gasoline or fuel oil.
Analogous corrosion problems occur in numerous other fields; for example, in the lubrication of internal combustion engines or steam engines including turbines, and other similar machinery, quantities of water are often as a result of the condensation of water from the atmosphere, or in the case of internal combustion engines as a result of dispersion or absorption in lubricating oil or water formed as a product of fuel compositions. Water, in such instances, corrodes the various metal parts of the machinery with which it comes in contact, the corrosion products causing further mechanical damages to bearing surfaces and the like due to their abrasive nature and catalytically promoting the chemical degradation of the lubricant. In this instance, as in the example cited above, the inhibitors known to the art have not always been entirely satisfactory, the organic material soluble inhibitors being, in general, relatively inefiective water corrosion inhibitors, and the water soluble inhibitors being difficult and in most instances impractical in their application. The same or similar problems arise in the preparation and use of various coating compositions such as greases, glass, household oils, paints, lacquers, Water soluble paints, etc., which are often applied to metal surfaces for protective or other purposes.
It is an object of this invention to provide potent corrosion inhibitors which are soluble in organic materials. A further object is to provide inhibitors of this type which will satisfactorily prevent corrosion of certain metal surfaces by water in contact with said organic materials and said'metal surfaces. Further objects are to provide water corrosion inhibitors which are stable at ordinary temperatures of use, easily and inexpensively prepared and which will not deleteriously affect organic materials with which they are incorporated. Other objects, together with some of the advantages to be derived when utilizing the inhibitors of the present invention, will become apparent from the following detailed description thereof.
In one embodiment the present invention relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material containing dissolved therein in minor proportion, but in amount sufiicient to inhibit corrosion of metal surfaces by said water, of a biguanide derivative.
In a more specific embodiment the present invention relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material having dissolved therein in minor proportion, but in amount suificient to inhibit corrosion of metal surfaces by said water, N-substituted biguanide.
In another specific embodiment the present invention relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material having dissolved therein in minor proportion, but in amount suflicient to inhibit corrosion of metal surfaces by said water, a N ,N -di-substituted biguanide.
In a more specific embodiment the present invention relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material having dissolved therein in minor proportion, but in amount suificient to inhibit corrosion of metal surfaces by said water, N -dodecylbiguam'de.
In still another more specific embodiment the present invention relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material having dissolved therein in minor proportion, but in amount sufficient to inhibit corrosion of metal surfaces by said water, N -phenyl-N -heptylbiguanide.
in another specific embodiment the present invention relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material having dissolved therein in minor proportion, but in an amount sufficient to inhibit corrosion of metal surfaces by said water, a 2,6-diamino-1,4-dihydro-l,3,5-triazine.
In another still more specific embodiment the present invention relates to a non-corrosive composition of matter comprising an organic material coming in contact with water during the useful life thereof, said organic material having dissolved therein in minor proportion, but in amount sufficient to inhibit corrosion of metal surfaces by said water, 2-amino-6-dodccylphenylamino-1,4-dihydro- 1,3,5-triazine.
It has been found, according to the present invention, that certain biguanide derivatives are excellent water corrosion inhibitors and are soluble in organic materials, thereby preventing corrosion of metal surfaces in contact with said organic material andwater. It has been found further that these biguanide derivatives, although probably soluble only in the organic material, prevent corrosion of the metal surfaces in contact with the water only, said water being in contact with said organic material.
Certain substituted biguanides for use in accordance with the present invention will have the following general structure:
where R is selected from the groups consisting of hydrocarbon and substituted hydrocarbon groups, and where R1, R2, and R3 are selected from the group consisting of hydrogen, hydrocarbon and substituted hydrocarbon groups.
In accordance with the established nomenclature the substituted biguanides are numbered as follows: Beginning with one of the terminal nitrogen atoms, in our case conveniently being the nitrogen atom at the left of the general structure, and numbering this nitrogen as 1, the remaining nitrogen atoms are numbered, reading from left to right, 2, 3, 4, and 5. Thus certain biguanide derivatives of the present invention require that one terminal nitrogen atom, number 1, be substituted by at least 1 hydrocarbon or substituted hydrocarbon group. As indicated in the general structure above, further substitution of the terminal nitrogen atoms may take place and this substitution may be such that both terminal nitrogen atoms, numbers 1 and 5, are each substituted by at least 1 hydrocarbon or substituted hydrocarbon group and may be completely substituted by hydrocarbon or substituted hydrocarbon groups.
This particular substitution is an essential feature of the present invention because it results, not only in a corrosion inhibitor which etfectively retards corrosion of metal surfaces in contact with an organic material and water, but also in a compound which is readily soluble in said organic material, and therefore, may be readily incorporated therein. As will be demonstrated further, in the examples, the readily solubility of the corrosion inhibitor in the organic material serves the function of providing a corrosion inhibitor which is effective in preventing corrosion of metal surfaces in contact both wit-h an organic material and with water in contact with said organic material.
Any suitable substituted biguanide may be used in accordance with the present invention. It generally is preferred that the additive compound contains at least 6 carbon atoms, although in some cases additives containing a fewer number of carbon atoms may be. used. N -substituted biguan'idcs containing 6. or more carbon atoms include N -hexylbiguanide, N -heptylbiguanide,
N -octylbiguanide, N -nonylbiguanide, N -decylbiguanide,
N undecylbiguanide, N dodecylbiguanide, N tri-' decylbiguanide, N tetradecylbiguanide, N pentadecylbiguanide, N hexadecylbiguanide, N heptadecylbiguanide, N octadecylbiguanide, N nonadecylbiguanide, etc., N -phenylbiguanide, N -tolylbiguanide, N -xylylbiguanide, N -naphthylbiguanide, N -ethylphenylbiguanide, N -propylphenylbiguanide, N -butylphenylbiguanide, N amylphenylbiguanide, N hexylphenylbiguanide, N -heptylphenylbiguanide, N -octylphenylbiguanide, N nonylphenylbiguanide, N decylphenylbiguanide, N -undecylphenylbiguanide, N -dodecy1- phenylbiguanide, N -tridecylphenylbiguanide, N -tetradecylphenylbiguanide, etc. Similar compounds in which the phenyl group is replaced by a naphthyl group, a substituted naphthyl group, a cyclohexyl group or a substituted cyclohcxyl group are similarly within the scope of the present invention.
Any suitable 1,5-substituted biguanide may be usedin accordance with the present invention. 1,5-substituted biguanides containing 6 or more carbon atoms include N -methyl-N -amylbiguanide, N -rnethyl-N -hexylbiguanide, N methyl-N -heptylbiguanide, N -methyl-N -octylbiguanide, N -methyl-N -nonylbiguanide, N -methyl-N decylbiguanide, N methyl N5 undecylbiguanide, N methyl-N -dodecylbiguanidc, N -methyl-N -tridecylbiguanide, N -methyl-N -tetradecylbiguanide, N -methyl-N pentadecylbiguanide, N -methyl-N -hexadecylbiguanide, N -methyl-N -heptadecylbiguanide, N -methyl-N octadecylbiguanide, N -methyl-N -nonadecylbiguanide, etc., N ethyl-N -butylbiguanide, N -ethyl-N -amylbiguanide, N -ethyl-N -hexylbiguanide, N -ethyl-N -heptylbiguanide, N -ethyl-N -octylbiguanide, N -ethyl-N -nonylbiguanide, N -ethyl-N -decylbiguanide, N -ethyl-N -undecylbiguanide, N -ethyl-N -dodecylbiguanide, N ethyl-N -tridecylbiguanide, N -ethyl-N -tetradecylbiguanide, N -ethyl-N pentadecylbiguanide, N ethyl N hexadecylbiguanide, etc., N -propyl-N -propylbiguanide, N -propyl-N -butylbiguanide, N -propyl-N -amylbiguanide, N -propyl-N hexylbiguanide, N -propyl-N -heptylbiguanide, N -propy1- N octylbiguanide, N propyl N nonylbiguanide, N propyl N decylbiguanide, N -propyl-N -undecylbiguanide, N -propyl-N -dodecylbiguanide, N -propyl-N -tridecylbiguanide, N -propyl-N -tetradecylbiguanide, N propyl-N -pentadecylbiguanide, etc., N -butyl-N -butylbiguanide, N -butyl-N -amylbiguanide, N -butyl-N -hexylbiguanide, N butyl N heptylbiguanide, N -butyl-N octylbiguanide, N -butyl-N -nonylbiguanide, N -butyl-N decylbiguanide, N -butyl-N -undecylbiguanide, N butyl N dodecylbiguanide, N -butyl-N -tridecylbiguanide, N -butyl-N -tetradecylbiguanide, N -butyl-N -pentadecylbiguanide, etc., N -amyl-N -amylbiguanide, N amyl-N -hexylbiguanide, N -amyl-N -heptylbiguanide, N amyl-N -octylbiguanide, N -amyl-N -nonylbiguanide, N amyl-N -decylbiguanide, N -amyl-N -undecylbiguanide, N -amyl-N -dodecylbiguanide, N -amylN -tridecylbiguanide, N -amyl-N -tetradecylbiguanide, N -amyl-N -pentadecylbiguanide, etc., and other N -alkyl-N -alkylbiguanides in which the total number of carbon atoms in the alkyl group is at least 6. The N -phenyl-N -a1kylbiguanides, N -t0lylN -alkylbiguanides, N -xylyl-N -alkylbiguam'dcs, N -naphthyl-N -alkylbiguanides, N -alkylphenyl- N -alkylbiguanides in which the first alkyl group may contain 2 or more carbon atoms, N -phenylalkyl- N -alkylbiguanides, and similar compounds in which the phenyl group is replaced by a naphthyl group, a substituted naphthyl group, cyclohexyl group, substituted cyclohexyl group, etc. are similarly within. the scope of the present invention. Other biguanides include N ,N -diphenylbiguanide, N -alkylphenyl- N -phenylbiguanide, N -alkylphenyl-N -alkylphenylbiguanides, N -phenylalkyl-N -phenylbiguanides, N -phenyl- 'nide, N ,N ,N ,N -tetracyclohexylalkylbiguanide, etc.
arsisov alkyl N alkylphenylbiguanides, N phenylalkyl N phenylalkylbiguanides, N -cyclohexyl-N -cyclohexylbiguanides, N -cyclohexyl-N -phenylbiguanides, N -cyclohexyl- N -phenylalkylbiguanides, N -cyclohexyl-N -alkylphenylbiguanides, N -alkylcyclohexyl-N -alkylcyclohexylbiguanides, N -alkylcyclohexyl-N -phenylbiguanides, N -cyclohexyl-N -phenylalkylbiguanides, N -alkylcyc1ohexy1-N alkylphenylbiguanides, N -cyclohexylalkyl-N -phenylbiguanides, N cyclohexylalkyl-N -phenylalkylbiguanides, N -cyclohexylalkyl-N -alkylphenylbiguanides, N -cyclo hexyl-N -alkylcyclohexylbiguanides, N -cyclohexyl-N cyclohexylalkylbiguanides, N -alkylcyclohexyl-N -alkylcyclohexylbiguanides, N -cyclohexylalkyl-N -alkylcyclohexylbiguanides, N -cyclohexylalkyl-N -cyclohexylalkylbiguanides, etc.
Trialkylbiguanides include those in which the N nitrogen atom is di-substituted and the N nitrogen atom is mono-substituted with hydrocarbon groups as hereinbe fore set forth. Typical compounds in this class include N ,N ,N triethylbiguanide, N propyl-N ,N -diethylbiguanide, N -butyl-N ,N -diethylbiguanide, etc., N -methyl- N ,N -dipropylbiguanide, N -ethyl-N ,N -d1propylb guanide, N N ,N -tripropylbiguanide, N -butyl-N ,N -d1propylbiguanide, etc., N -n1ethyl-N ,N -dibutylbiguanide, N ethyl-N ,N -dibutylbiguanide, N ,N ,N -tr1butylb1guamde, N -amyl-N ,N -dibutylbiguanide, N -hexyl-N ,N :d1butylbiguanide, etc., N -phenylN ,N -dimethylbiguamde, N ph'enyl-N ,N -diethylbiguanide, etc., N -phenyl-N -methyl- N -ethylbiguanide, N -phenyl-N -methylN -propylb1guanide, etc., N -phenyl-N ,N -dipropylbiguanide, N -phenyl- N -propyl-N -butylbiguanide, N -phenyl-N ,N -dibutylbiguanide, N -phenyl-N ,N -diamylbiguanide, N -phenyl- N ,N -dihexylbiguanide, etc., N -tolyl-N ,N -dimethy1b1- guanide, N -tolyl-N -methyl-N -ethylbiguanide, N -tolyl- N ,N -diethy1biguanide, N -tolyl-N -ethyl-N -propylb1guanide, N tolyl N ,N dipropylbiguanide, N -tolyl-N propyl N butylbiguanide, N -tolyl-N ,N -dibutylbiguanide, 'etc., N -xylyl-N ,N -dialkylbiguanides, N -alkylphenyl-N ,N -dialkylbiguanides, N -phenylalkyl-N ,N dialkylbiguanides, N -cyclohexylalkyl-N ,N -dialkylb1guanides, N -cyclohexyl-N ,N -dialkylbiguanides, N -pheny1- N -phenyl-N -alkylbiguanides, N ,N ,N -triphenylbiguanides, N -pheny1-N -phenyl-N -alkylphenylbiguanides, N phenyl-N -phenyl-N -phenylalkylbiguanides, N -phenyl- N ,N phenylalkylbiguanides, N phenyl-N ,N alkylphenylbiguanides, N alkylphenyl N phenyl-N -alkylphenylbiguanides, N phenylalkyl N -phenyl-N alkylphenylbiguanides, N ,N ,N triphenylalkylbiguanldes, N ,N ,N -trialkylphenylbiguanides, etc.
N ,N ,N ,N -tetra-substituted-biguanides are within the scope of the present invention and the substituent groups may comprise alkyl, phenyl-phenylalkyl, alkylphenyl, cyclohexyl, alkylcyclohexyl, and cyclohexylalkyl groups. Particularly preferred compounds include those in which the substituent group is the same because this simplifies manufacture of the compounds and thus include N ,N N ,N -tetraethylbiguanide, N ,N ,N ,N -tetrapropylbiguanide, N ,N ,N ,N -tetrabutylbiguanide, N ,N ,N ,N -tetraamylbiguanide, N ,N ,N ,N -tetrahexylbiguanide, N ,N N ,N -tetraheptylbiguanide, etc., N ,N ,N ,N -tetraphenylbiguanide, N ,N ,N ,N -tetraalkylphenylbiguanide, N ,N N ,N -tetraphenylalkylbiguanide, N ,N ,N ,N tetracyclohexylbiguanide, N ,N ,N ,Nitetraalkylcyclohexylbiguais to be understood, however, that these substituent groups may be different as, for example, such compounds as N ,N -diphenylbiguanide, N ,N -dibutylbiguanide, N ,N ditolylbiguanide, N ,N -diamylbiguanide, N ,N ,N -triphenyl-N -butylbiguanide, etc.
These biguanide derivatives may be prepared in any suitable manner. For example, N -phenyl-N -heptylbiguanide may be prepared by commingling the desired aryl-diazonium halide with dicyandiamide and decompoing the resultant product to aryl-dicyandiamide, which is reacted with primary heptyl amine in the presence of copper sulfate. When a tri-substituted biguanide is desired, a secondary amine is employed. The tetrasubstituted biguanides may be prepared by the reaction of two molecular proportions of the desired amine hydrochloride with sodium dicyanamide.
Other biguanide derivatives which are within the scope of the present invention are the 2,6-diamino-1,4-dihydro- 1,3,5-triazines which may be illustrated by the following general formula:
where again, R may be selected from hydrocarbon and substituted hydrocarbon groups, R1, R2 and R3 may be selected from the hydrogen, hydrocarbon and substituted hydrocarbon groups, and R4 may be selected from hydrogen, hydrocarbon and substituted hydrocarbon groups. Compounds of this structure include 2-arnino-6-dodecylphenylamino-l,4-dihydro-1,3,5-triazine, 2-amino-4-phenyl- 6 dodecylphenylamino 1,4 dihydro 1,3,5 triazine, 2- amino 4 n propyl-6-dodecylphenylamino-1,4-dihydro- 1,3,5-triazine, Z-amino-4-isopropyl-6-dodecylphenylamino- 1,4 dihydro 1,3,5 triazine, 2-amino-4-butyl-6-dodecylphenylamino-1,4-dihydro-1,3,5-triazine, 2-amino-4-amyl- 6-nonylphenylamino-1,4-dihydro-1,3,5-triazine, 2-amino- 4 hexyl 6-hexylphenylamino-1,4-dihydro-1,3,5-triazine, etc.
1,4-dihydro-1,3,5-triazines may be prepared by the reaction of biguanides with aldehydes. When substituted dihydro-1,3,5-triazines are desired, the biguanide is suitably substituted. Thus in the preparation of the preferred 2-arnino-4-n-propyl-6-dodecylphenylamino 1,4 dihydro- 1,3,5-triazine, dodecylphenylbiguanide is reacted with butyraldehyde, the reaction being efiected by merely boiling equimolecular quantities of the components or solutions thereof, with constant water separation.
It is to be understood that the corrosion inhibitors of the present invention may comprise the specific compounds named above alone or in admixture with various isomers thereof. Furthermore, it is understood that the various corrosion inhibitors which may be utilized in accordance with the present invention are not necessarily equivalent for use in the inhibition of difierent organic compounds which may be treated in accordance with the present invention. Furthermore, it is understood that the particular additive to be used should be selected so as to meet the specific requirements of the particular material being stabilized. For example, in the treatment of fuel oil, the R group should be selected so that the additive contains a total of from about 6 to about 30 carbon atoms permole in order that the additive may not be too volatile, will be readily soluble, etc. It is appreciated that the particular selection of the substituent groups will depend upon the particular organic material in which the additive is to be employed.
The presently described inhibitors are most effective in preventing water corrosion of ferrous metals, aluminum, nickel, chromium, and alloys of these metals. To a lesser extent, the biguanide derivative inhibitors are also beneficial in preventing Water corrosion of copper and copper alloys.
The inhibitors of the present invention may be incorporated into any organic material, whether solid, semisolid or liquid in which they are soluble and with which Thus they may be added to hydrocarbons (which may be paraffinic, olefinic, naphthenic, or aromatic) of the type described, or to chlorinated hydrocarbons, alcohols, esters, ethers, ketones, nitriles, amino compounds, amides, fats and fatty oils (edible and non-edible) paints, varnishes, natural waxes, oils, etc.
When adding the inhibitors to hydrocarbon oils such as gasoline, benzene, kerosene, fuel oils, cycle stocks, etc., 0.0001 to 0.5% by weight of the biguanide derivative will generally be found satisfactory for inhibition of water corrosion, although lower or higher amounts may be used. The precise amount of inhibitor to be utilized in each instance will, of course, vary with the particular conditions at hand and should be determined experimentally, particularly when usually severe corrosion conditions are to be overcome. However, in the majority of practical applications when handling substantially water insoluble organic materials of this type, the addition of approximately 0.001 to about 0.1% by weight of the inhibitor will be found satisfactory.
Larger amounts of inhibitor up to about 2.0% by weight may be required for inhibiting other organic materials, particularly those miscible with water, such as alcohols, ketones and the like, as for example, methyl alcohol, ethyl alcohol, propyl alcohol, acetone, methyl ethyl ketones, methyl vinyl ketone, dioxane, etc.
Among other suitable applications for the present inthey do not react.
vention, the following come into consideration. For
slushing oils and other rust preventive coatings, the biguanide derivatives will be found effective as corrosion inhibitors for most practical applications, when incorporated into the coatings in amounts ranging approximately as follows: Oil base coatings, 0.01% to 1% by weight; wax base coatings, other petroleum wax (petrolatum) base coatings, 0.001% to 1% by weight; petroleum wax base coatings, 0.01% to 5% by weight or higher based on the petroleum wax contained in the particular coating; a primer coating for paint, 0.01% to 1.0% by weight based on the dry constituents; lubricant compositions such as lubricating oils for internal combustion engines, turbines and the like, greases, semi-greases, etc., 0.001% to about 1.0% by weight; general purpose oils, such as household oils, 0.01% to 1.0%.
The following specific examples serve to illustrate the effectiveness of the presently disclosed corrosion inhibitors. The procedure used in each of the following examples is given as follows: The samples were stored in clear 4 ounce bottles in a 100 F. constant temperature room in the absence of light. To make up a sample, 50 grams of an oil was placed in the bottle, together with 5 ml. of distilled water or synthetic sea water. By weight, 0.01% of the corrosion inhibitor was added to the oil; the corrosion inhibitor had previously been dissolved in benzene or isopropyl alcohol in a ratio of 0.0050 grams per milliliter of solvent, and thereby the oil could accurately be inhibited by using 1 ml. of the solvent solution from a pipette. An iron strip was then added, the bottle corked and thoroughly shaken. Before storing the cork was loosened in order to allow air to enter. The iron strips were cut from mild carbon steel; the bluing was removed by dilute acid pickling with constant movement. They were then rinsed in water several times, immersed in acetone, and air dried in a low temperature oven (about 100 C.). A light film of rust formed almost instantly while drying; just before placing the iron strips in the sample bottle the strips were buifed using a motor driven iron wire wheel. The strips were not permitted to contact the skin after the pickling operation; while buffing they were held with a towel with one end while bufiing the other end, then reversed still using the towel to hold them. It was noticed in previous work that if the strips were touched by the fingers, the oil from the skin adheres thereto and forms corrosion at the point of contact and thereby prevents accurate observation of results.
After storage periods of 2, 5 and 30 days in a 100 F. room, visual observations were taken of the samples to determine approximately the amount of corrosion which had taken place. Amounts of corrosion were classed as negative, trace, slight, medium, and heavy, and were noted on the iron strip within the oil level and also in the water layer where usually it floated free in small particles and a brown haze or sludge developed as the deposit grew. Loose rust tended to break away from the strip in the oil level and settle down into the water level. In a few cases, the rust on the strip in the oil level was fine and adherent to the strip, occurring as a more or less dense layer. In most cases, the oil phase corrosion occurred around small droplets of water which cling to the strip after the original shaking; in such cases the rust was very loose and easily broken free; considerable pitting of the iron strips was noted beneath such bubbles of water and rust. No attempt was made to determine quantitatively the amounts of metal rust due to the two varieties of corrosion. Heavy pitting of the iron strip also tended to concentrate in the water layer. In almost all cases rusting took place on that part of the iron strip which extended into the air in the bottle above the oil level, although in cases of negative to slight rusting, the air rust was reduced. A milky haze was noted in the water layer of several of the samples which had negative or trace corrosion results; it was speculated that perhaps the corrosion inhibitor in these cases was ex tracted from the oil by the water and thus caused the water to become hazy. The following results were obtained:
Example I Cracked Oil with Distilled H2O Rust on Rust Rust on Rust; Rust on Rust Common :51 5 2? 091% by Strip in Loose in Strip in Loose in Strip in Loose in g 011 Level H O Oil Level H20 011 Level H1O After 2 days After 5 days After 30 days 1. Blank slight. slight.... slight medium sligliL... medium. 2. Armeen 12D biguanide negative. negative. negative. negative. negative. negative. 3. Armeen C biguanide o"... on... do. ..do. ..do. Do. 4. N -phenylbiguanide 0 do. ..d0. 0..... .do Do. 5. N -p-toly1-N ,N -di-n-butybbiguado trace- -..do slight... tracemedium.
m'de. 6. Z-amino-fi-dodecylphenylamino-l, trace. negative. trace. trace. .do trace.
4-dihydro-1,3,5-triazine.
a Armeen 12D is a commercially available mixture of alkyl amines, predominately On, which has been purified by fractionation; the water layer under the oil in this case was b Armeen C is a commercially available mixture of alkyl amines, predominately C12.
Example II Virgin Oil with Distilled H10 v Rust on Rust Rust on Rust Rust on Rust az gg by Strip in Loose m Strip in Loose in Strip in Loose m 8 Oil Level 11.0 on Level Hlo Oil Level mo After 2 days After 5 days After 30 days 1. Blank... slight... medium. medium medium. medium. medium. 2. Armeen 12D biguanide negative. negative. negative. negative. trace.... negative 3. Armeen C biguanide do.. .-.do..... trace-... ...do...-. o-.--. trace. 4. N -phenylbiguanide do..--- slight.-.. negative. slight.--. negati negative 5. N -nonylnaphthyl-biguanide-... trace.... negativev sllg trace--.. slight... slight. 6. N -phenyl-N -nbutylbiguanide.. negative. 0..... negative. negative. negative. negative 7. N -phenyl-N -n-hepty1biguanide. ace. 8. N -p-tolyl-N -n-buty1biguanide negative 9. 2 amino-i-phenyl-G-phenyltrace..... slight.
amino 1,4 dillydro 1,3,5 triazine. 10. 2-amino-6-dodecylphenylamino- -..do..-.. negative. do....- trace.-.- negative. Do.
l,4-dihydro-1,3,6-triazine.
1 Water layer clear. b Water layer milky. Water layer clear. 5 Water layer milky.
Example 111 Cracked Oil with Synthetic Sea H10 Rust on Rust Rust on Rust Rust on Rust 00170310 i i 001% by Strip in Loose in Strip in Loose in Strip in Loose in We g Oil Level Hoo Oil Level 11,0 on Level mo After 2 days After 5 days After days 1. Blank heavy..- heavy... heavy--- heavy. 2. Armeen 12D biguanl trace-... traee---. trace-... slight. 3. Armeen C biguanide..-.. sligbt.... ...do..-.. slight.... Do. 4. N -phenyl-N -n-heptylbiguanida --do..-.. slight-.. medium. medium. 5. 2-amino-6-dodecylphenylaminomedium. medium. ...do....- Do.
1,4-d.lhydro-1,3,5-triazine.
Example IV Virgin Oil with Synthetic Sea Water Rust on Rust Rust on Rust Rust on Rust corrosion gg by Strip in Loose in Strip in Loose in Strip in Loose in we 011 Level H on Level rrlo Oil Level Hlo After 2 days After 5 days After 30 days 1. Blank heavy-.- heavy... heavy... heavy. 2. Armeen 12D biguani slight.... slight.... slight... medium. 3. Armeen O biguanide- .do....- ---do slight. 4. N -phenylbiguanide traco--.. trace-... Do. 5. N --pl1enyl--N -n-heptylbiguanide. slight.--. slight.-.. medium.
We claim as our invention:
1. In the handling of organic materials wherein the organic material contacts metal surfaces in the presence of water, the method of inhibiting corrosion of the metal surfaces by said water which comprises dissolving in the organic material from about 0.0001% to about 2% by weight of asubstituted biguanide having a hydrocarbon substituent on at least one of its terminal nitrogen atoms, said organic material and said substituted biguanide being mutually soluble and non-reactive.
2. In the handling of organic materials wherein the organic material contacts metal surfaces in the presence of water, the method of inhibiting corrosion of the metal surfaces by said water which comprises dissolving in the organic material from about 0.0001% to about 2% by weight of a substituted biguanide having a hydrocarbon substituent on each of its terminal nitrogen atoms, said organic material and said substituted biguanide being mutually soluble and non-reactive.
3. In the transportation and storage of hydrocarbon oils where the oil contacts metal surfaces in the presence of water, the method of inhibiting corrosion of the metal surfaces by said water which comprises dissolving in the hydrocarbon oil from about 0.0001% to about 2% by weight of a substituted biguanide having a hydrocarbon substituent on at least one of its terminal nitrogen atoms.
4. In the transportation and storage of hydrocarbon oils where the oil contacts metal surfaces in the presence of water, the method of inhibiting corrosion of the metal surfaces by said water which comprises dissolving in the hydrocarbon oil from about 0.0001% to about 2% by weight of a substituted biguanide having a hydrocarbon substituent on each of its terminal nitrogen atoms.
5. The method of claim 3 further characterized in that said substituted biguanide is an N-alkylbiguanide.
6. The method of claim 3 further characterized in that said substituted biguanide is an N-dodecylbiguanidc.
7. The method of claim 3 further characterized in that said substituted biguanide is an N-dodecylphenylbiguanide.
8. The method of claim 3 further characterized in that said substituted biguanide is an N ,N -di-alkylbiguanide.
9. The method of claim 4 further characterized in that said substituted biguanide has an alkyl substituent on one of its terminal nitrogen atoms and an aryl substituent on the other terminal nitrogen atom.
10. The method of claim 4 further characterized in that said substituted biguanide has an alkyl substituent on one of its terminal nitrogen atoms and an alkylaryl substituent on the other terminal nitrogen atom.
11. The method of claim 4 further characterized in that said substituted biguanide is N -phenyl-N -heptylbiguanide.
References Cited in the file of this patent UNITED STATES PATENTS
Claims (1)
- 3. IN TH TRANSPORTATION AND STORAGE OF HYDROCARBON OILS WHERE THE OIL CONTACTS METAL SURFACES IN THE PRESENCE OF WATER, THE METHOD OF INHIBITING CORROSION OF THE METAL SURFACES BY SAID WATER WHICH COMPRISES DISSOLVING IN THE HYDROCARBON OIL FROM ABOUT 0.0001% TO ABOUT 2% BY WEIGHT OF A SUBSTITUTED BIGUANIDE HAVING A HYDROCARBON SUBSTITUENT ON AT LEAST ONE OF ITS TERMINAL NITROGEN ATOMS.
Publications (1)
Publication Number | Publication Date |
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US2734807A true US2734807A (en) | 1956-02-14 |
Family
ID=3444276
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US2734807D Expired - Lifetime US2734807A (en) | Biguanide derivatives as corrosion |
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US (1) | US2734807A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3152181A (en) * | 1961-01-18 | 1964-10-06 | Us Vitamin Pharm Corp | Alkoxypropylene biguanides |
US3168519A (en) * | 1961-10-17 | 1965-02-02 | American Cyanamid Co | 1-alkylphenyl-2, 2-di lower alkyl-4, 6-diimino-hexahydro-s-triazines |
US3170925A (en) * | 1965-02-23 | L-subsmtuted | ||
US3183230A (en) * | 1961-01-13 | 1965-05-11 | Us Vitamin Pharm Corp | Haloaralkyl biguanides |
US3296135A (en) * | 1963-02-08 | 1967-01-03 | Union Carbide Corp | Lubricant compositions having improved corrosion and oxidation properties |
US3909200A (en) * | 1967-05-22 | 1975-09-30 | Petrolite Corp | Use of guanidine derived compounds as corrosion inhibitors |
US4201599A (en) * | 1978-07-06 | 1980-05-06 | Trevor Morgans | Restoration and protection of cutting surfaces |
JPWO2010024225A1 (en) * | 2008-08-25 | 2012-01-26 | 浜理薬品工業株式会社 | New dihydrotriazine derivatives |
CN110615886A (en) * | 2019-09-05 | 2019-12-27 | 哈尔滨工程大学 | Biguanide derivative antibacterial epoxy resin curing agent and preparation method thereof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2043257A (en) * | 1933-10-09 | 1936-06-09 | Stauffer Chemical Co | Preservation of chlorinated hydrocarbons |
US2373021A (en) * | 1943-02-05 | 1945-04-03 | Du Pont | Stabilization of petroleum hydrocarbons |
US2469745A (en) * | 1946-06-21 | 1949-05-10 | Standard Oil Dev Co | Stabilizing aromatic amines |
US2627504A (en) * | 1948-07-14 | 1953-02-03 | Monsanto Chemicals | Dielectric containing halogenated aromatic hydrocarbon and mono ortho tolyl biguanide as corrosion inhibitor |
-
0
- US US2734807D patent/US2734807A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2043257A (en) * | 1933-10-09 | 1936-06-09 | Stauffer Chemical Co | Preservation of chlorinated hydrocarbons |
US2373021A (en) * | 1943-02-05 | 1945-04-03 | Du Pont | Stabilization of petroleum hydrocarbons |
US2469745A (en) * | 1946-06-21 | 1949-05-10 | Standard Oil Dev Co | Stabilizing aromatic amines |
US2627504A (en) * | 1948-07-14 | 1953-02-03 | Monsanto Chemicals | Dielectric containing halogenated aromatic hydrocarbon and mono ortho tolyl biguanide as corrosion inhibitor |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3170925A (en) * | 1965-02-23 | L-subsmtuted | ||
US3183230A (en) * | 1961-01-13 | 1965-05-11 | Us Vitamin Pharm Corp | Haloaralkyl biguanides |
US3152181A (en) * | 1961-01-18 | 1964-10-06 | Us Vitamin Pharm Corp | Alkoxypropylene biguanides |
US3168519A (en) * | 1961-10-17 | 1965-02-02 | American Cyanamid Co | 1-alkylphenyl-2, 2-di lower alkyl-4, 6-diimino-hexahydro-s-triazines |
US3296135A (en) * | 1963-02-08 | 1967-01-03 | Union Carbide Corp | Lubricant compositions having improved corrosion and oxidation properties |
US3909200A (en) * | 1967-05-22 | 1975-09-30 | Petrolite Corp | Use of guanidine derived compounds as corrosion inhibitors |
US4201599A (en) * | 1978-07-06 | 1980-05-06 | Trevor Morgans | Restoration and protection of cutting surfaces |
JPWO2010024225A1 (en) * | 2008-08-25 | 2012-01-26 | 浜理薬品工業株式会社 | New dihydrotriazine derivatives |
CN110615886A (en) * | 2019-09-05 | 2019-12-27 | 哈尔滨工程大学 | Biguanide derivative antibacterial epoxy resin curing agent and preparation method thereof |
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