US2339797A - Lubricating oil - Google Patents
Lubricating oil Download PDFInfo
- Publication number
- US2339797A US2339797A US359105A US35910540A US2339797A US 2339797 A US2339797 A US 2339797A US 359105 A US359105 A US 359105A US 35910540 A US35910540 A US 35910540A US 2339797 A US2339797 A US 2339797A
- Authority
- US
- United States
- Prior art keywords
- compounds
- lubricating oil
- lecithin
- aromatic
- derivatives
- 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
- 239000010687 lubricating oil Substances 0.000 title description 25
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 19
- 239000000787 lecithin Substances 0.000 description 19
- 229940067606 lecithin Drugs 0.000 description 19
- 235000010445 lecithin Nutrition 0.000 description 19
- 150000001491 aromatic compounds Chemical class 0.000 description 14
- -1 aryl phosphites Chemical class 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 5
- 239000010802 sludge Substances 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Chinese gallotannin Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- 125000005456 glyceride group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000005189 alkyl hydroxy group Chemical group 0.000 description 2
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229940079877 pyrogallol Drugs 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- 125000005425 toluyl group Chemical group 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YBQZXXMEJHZYMB-UHFFFAOYSA-N 1,2-diphenylhydrazine Chemical compound C=1C=CC=CC=1NNC1=CC=CC=C1 YBQZXXMEJHZYMB-UHFFFAOYSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical class C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- RMKRCLBDIMSFQB-UHFFFAOYSA-N 4-amino-2-benzylphenol Chemical compound NC1=CC=C(O)C(CC=2C=CC=CC=2)=C1 RMKRCLBDIMSFQB-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UHFFFAOYSA-N Rohrzucker Natural products OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- XIWMTQIUUWJNRP-UHFFFAOYSA-N amidol Chemical compound NC1=CC=C(O)C(N)=C1 XIWMTQIUUWJNRP-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- HHTWOMMSBMNRKP-UHFFFAOYSA-N carvacrol Natural products CC(=C)C1=CC=C(C)C(O)=C1 HHTWOMMSBMNRKP-UHFFFAOYSA-N 0.000 description 1
- 235000007746 carvacrol Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- PONXTPCRRASWKW-KBPBESRZSA-N diphenylethylenediamine Chemical compound C1([C@H](N)[C@@H](N)C=2C=CC=CC=2)=CC=CC=C1 PONXTPCRRASWKW-KBPBESRZSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- WYXXLXHHWYNKJF-UHFFFAOYSA-N isocarvacrol Natural products CC(C)C1=CC=C(O)C(C)=C1 WYXXLXHHWYNKJF-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical class C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 1
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- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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Definitions
- the present invention relates to the improvement of lubricating oils.
- aryl phosphites, triphenyl phosphites and hydroxy and/or amino aromatic compounds do not function most satisfactorily in lubricating oils to inhibit the formation of sludge and to reduce the tendency of the lubricating oil toward producing corrosion on metal surfaces.
- polyhydroxy, pclyamino, alkylhydroxy and hydroxyamino nuclear compounds Although it is preferred to use the polyhydroxy, pclyamino, alkylhydroxy and hydroxyamino nuclear compounds, it also has been found satisfactory to use even poly-nuclear monohydroxy or moncamino compounds.
- the preferred compounds that may be employed in combination with the lecithin for addition to the lubricating oil followed by an elevated temperature treatment are compounds generally included in the groups of the alkyl phenols, alkyl naphthols, di-substituted hydroxylated or aminated benzenes or naphthalenes, alkoxy phenols or naphthols, di and poly phenyl, toluyl, naphthyl or other aryl amines, amino phenols, alkylated or alkoxylated or hydroxylated tol nes or zylenes.
- polynuclear aromatic hydrocarbons or their derivatives such hydrocarbons containing at least 3 nuclei or even hydrocarbons of the nature of the naphthenes or terpenes or their various carboxylated, hydroxylated, alkylated or alkoxylated derivatives.
- the preferred compounds are, however, hydroquinone, pyrogallol, ethyl or butyl pyrogallol, guaiacol, quinone, phloroglucinol, catechol or p-yrocatechin, tributyl catechol, triamyl catechol, eugenol, vanillin,- carvacrol, thymol, tannins, gallic acid, gallo-tannin, tannic acid, alphanaphthol, betanaphthol, ortho or, para cresol, naphthoquinone, phenylbetanaphtylamine, alpha or beta naphthylamines, p-aminophenol, p-aminosaligenin, 2,4-di-aminophenol, monobenzyl-p-aminophenol, diphenylethylenediamine, benzyl-m-p-henylenediamine, p-aminodimethyl
- aromatic acids may be utilized, particularly aromatic carboxy acids containing one or more amino groups or hydroxy groups either in the nucleus or in aliphatic side chains, such as cinnamic, benzoic, salicylic or phthalic acids.
- This lecithin preferably should be added to or combined with the aromatic compounds in amounts varying from 5 to 30 parts of lecithin for each 20 parts of the aromatic compound.
- the lecithin when mixed with the aromatic compounds should preferably contain between 10% and 60% of a glyceride oil, preferably a vegetable glyceride oil.
- This combination of lecithin and the aromatic compounds, and prefefibly the glyceride oil, with or without heating before addition, is mixed with the lubricating oil and thoroughly dispersed therethrough, the lubricating oil during the addition or after the addition being heated with agitation to a temperature in excess of 350 F. and desirably to between 400 F. and 600 F.
- an equal mixture of the lecithin and the aromatic compound by weight is employed rather than other proportions as it has generally been found that where an equal mixture of the lecithin and the aromatic compound is prepared and added to the lubricating oil during or followed by the elevated temperature treatment, the most desirable effect on the lubricating oil is obtained.
- Monoamino-aryl compounds such as aniline, diphenylamine, acetanilide, acetalaniline, dimethylaniline, amino-diphenyl, benzidine and their derivatives;
- Amine condensation products with aldehydes and ketones such as benzalanilines, formylalphanaphthylamine, butyraldehyde-aniline, aldolaniline and their derivatives;
- Nitrogen or oxygen ring compounds such as furfural, furfuryl alcohol, furoic acid, diphenylguanidine, p-dimethylamino-phenyl-pphenetidylguanidine, pyridine, acridine, triazine, piperidine, quinoline, uric acid, urea, morpholine and their derivatives;
- Sulphur compounds such as thiodiphenylamine, methyl, ethyl, benzyl or phenyl sulphides or mercaptans, phenyl disulphide, benzyl sulphide and their derivatives;
- Aliphatic amines such as dimethylamine, glutamic acid, glycine, triamylamine, n-butyldiamylamine, benzyldiethylamine and their derivatives;
- Terpenes or lignin materials such as terpentine, pinene, abietic acid or various crude mixtures containing the same such as tallol, pine oil, rosin oil or their derivatives.
- esters or salts in which a metal forms part of the acid radical for example, such compounds as the phenyl, benzyl, toluyl, cresyl, ethyl, amyl, butyl, propyl and other aryl or alkyl esters of acids including antimony, bismuth, tungsten, chromium, vanadium, thorium, molybdenum, tantalum, columbium, manganese and, less preferably, metals such as iron, lead, tin, or zinc, these metals in all cases preferably all being in a state less than their maximum oxidized state and in ous condition so as to form ites although in some instances the ic acids may be utilized which will form the ates.
- these compounds preferably have an oxygen atom linking the metal to the carbon of the alkyl or aryl group, it is also possible to use similar compounds in which the carbon is linked directly to the metal atom or in which the intermediate linkage is by way of a sulfur atom rather than an oxygen atom.
- lecithin is preferred for use in accordance with this invention, it is possible to use cephalin and other similar phosphatides of plant or animal origin.
- cephalin and other similar phosphatides of plant or animal origin.
- nerve or brain tissue and meat scrap residues There may also be utilized nerve or brain tissue and meat scrap residues, alcohol and hydrocarbon soluble extracts of crude sugars such as crude cane or beet sugar or their residues such as blackstrap molasses, for combination with the aromatic compound and lubricating oil.
- the stabilizing procedures of the present invention are most applicable to non-volatile high molecular weight aliphatic hydrocarbons, and these procedures may also be utilized with high boiling liquid hydrocarbon mixtures derived from other sources than petroleum and even in some instances they may be used with solid high molecular weight hydrocarbon mixtures.
- these stabilizing procedures may be employed with non-aliphatic hydrocarbons of high boiling point and still less preferably with high molecular Weight glyceride oils, particularly the triglycerides of high molecular Weight fatty acids having 12 to 36 carbon atoms, which acids may contain if desired one or more double bonds or hydroxy groups.
- the invention is not as desirably applicable to hydrocarbons of vegetative origin such as rubber or latex and is not particularly applicable to hydrocarbon compounds of volatile nature or having a boiling point less than about 200 F. to 250 F.
- a process of improving lubricating oils consisting substantially of the non-volatile high molecular weight aliphatic hydrocarbons to decrease sludge formation and also to decrease their tendency to cause corrosion of metal surfaces which comprises treating the entire body of such oil with a relatively small amount of a combination of lecithin and p-cresol at an elevated temperature in excess of 350 F.
- a process of improving lubricating oils consisting substantially of the non-volatile high molecular weight aliphatic hydrocarbons to decrease sludge formation and also to decrease their tendency to cause corrosion of metal surfaces which comprises treating the entire body of such oil with a relatively small amount of a combination of a phosphatide and p-cresol at an eievated temperature in excess of 350 F.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
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- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
Patented Jan. 25, 1944 LUBRICATING OIL Sidney Masher, New York, N. Y., assignor to Musher Foundation, Incorporated, New York, N. Y., a corporation of New York No Drawing. Application September 30, 1940, Serial No. 359,105
2 Claims.
The present invention relates to the improvement of lubricating oils.
It is among the objects of the present invention to provide improved lubricating oils which Will have a decreased tendency toward sludge formation and which will have lessened tendency to cause corrosion of metallic surfaces with which such lubricating oils may come in contact.
Still further objects and advantages will appear from the more detailed description set forth below, it being understood, however, that this more detailed description is given by Way of illustration and explanation only, and not by Way of limitation, since various changes therein may be made by those skilled in the art Without departing from the scope and spirit of the present invention.
It has been found that aryl phosphites, triphenyl phosphites and hydroxy and/or amino aromatic compounds do not function most satisfactorily in lubricating oils to inhibit the formation of sludge and to reduce the tendency of the lubricating oil toward producing corrosion on metal surfaces.
It has however been found that combinations of lecithin with certain aromatic hydroxy compounds and amino compounds and particularly hydroxylated and alkylated, polyhydroxy, polyamino and aminohydroxy compounds are most effective and surprisingly active in stabilizing lubricating oils at elevated temperatures.
Although it is preferred to use the polyhydroxy, pclyamino, alkylhydroxy and hydroxyamino nuclear compounds, it also has been found satisfactory to use even poly-nuclear monohydroxy or moncamino compounds.
Among the preferred compounds that may be employed in combination with the lecithin for addition to the lubricating oil followed by an elevated temperature treatment are compounds generally included in the groups of the alkyl phenols, alkyl naphthols, di-substituted hydroxylated or aminated benzenes or naphthalenes, alkoxy phenols or naphthols, di and poly phenyl, toluyl, naphthyl or other aryl amines, amino phenols, alkylated or alkoxylated or hydroxylated tol nes or zylenes.
Less preferably there may be employed polynuclear aromatic hydrocarbons or their derivatives, such hydrocarbons containing at least 3 nuclei or even hydrocarbons of the nature of the naphthenes or terpenes or their various carboxylated, hydroxylated, alkylated or alkoxylated derivatives. The preferred compounds are, however, hydroquinone, pyrogallol, ethyl or butyl pyrogallol, guaiacol, quinone, phloroglucinol, catechol or p-yrocatechin, tributyl catechol, triamyl catechol, eugenol, vanillin,- carvacrol, thymol, tannins, gallic acid, gallo-tannin, tannic acid, alphanaphthol, betanaphthol, ortho or, para cresol, naphthoquinone, phenylbetanaphtylamine, alpha or beta naphthylamines, p-aminophenol, p-aminosaligenin, 2,4-di-aminophenol, monobenzyl-p-aminophenol, diphenylethylenediamine, benzyl-m-p-henylenediamine, p-aminodimethylaniline, m-toluidine, diphenylhydrazine and tyrosine. These various materials are included in the expression substituted aranes.
Less preferably, aromatic acids may be utilized, particularly aromatic carboxy acids containing one or more amino groups or hydroxy groups either in the nucleus or in aliphatic side chains, such as cinnamic, benzoic, salicylic or phthalic acids.
It is, of course, possible to use derivatives of the above identified compounds in which one or more of the hydrogen atoms in the benzene or naphthalene nucleus or in the aliphatic side chain or in the amino or hydroxy groups, is or are replaced by alkyl, aryl, hydroxy, amino, alkoxy, keto, aldo or nitro groups although this is usually not preferred.
This lecithin preferably should be added to or combined with the aromatic compounds in amounts varying from 5 to 30 parts of lecithin for each 20 parts of the aromatic compound.
The lecithin when mixed with the aromatic compounds should preferably contain between 10% and 60% of a glyceride oil, preferably a vegetable glyceride oil.
This combination of lecithin and the aromatic compounds, and prefefibly the glyceride oil, with or without heating before addition, is mixed with the lubricating oil and thoroughly dispersed therethrough, the lubricating oil during the addition or after the addition being heated with agitation to a temperature in excess of 350 F. and desirably to between 400 F. and 600 F.
It has been found that the interaction of the lubricating oil, lecithin and the aromatic compound is not most satisfactorily obtained unless the high heat treatment is applied to the lubricating oil after or during addition of the combination of lecithin and the aromatic compound, and it has been particularly found desirable that such heat treatment should be conducted'with substantial agitation for a period of at least 10 minutes and the treatment may be conveniently .continuedforas long as severalhoursor more.
UUQI U" "W"! This is quite surprising due to the fact, that normally lubricating oils, as well as lecithin, are decomposed or broken down and rendered more subject to deterioration as a result of being subjected to such elevated temperatures. In accordance with this invention it is necessary for the lubricating oil to be subjected to the elevated temperature in excess of 350 F. together with and after having had thoroughly admixed therein the combination of the lecithin and the aromatic compound in order to develop the desired effect upon the lubricating oil.
It is not known whether the heat treatment of the lubricating oil containing the lecithin and the aromatic compound results in a chemical action between the lecithin and aromatic compound or the lubricating oil or whether a special kind of catalytic action takes place, but the heat treatment is necessary in order to obtain the desired efiect upon the lubricating oil to retard sludge formation and corrosive tendencies of the oil.
It has been found most satisfactory to add the combination of lecithin and the aromatic compound in amounts varying from 0.075% to as much as 0.75% although generally between 0.2% and 0.'l% are sufficient to show a marked effect upon the lubricating oil that is treated at the elevated temperature with the combination of lecithin and the aromatic compound.
Preferably an equal mixture of the lecithin and the aromatic compound by weight is employed rather than other proportions as it has generally been found that where an equal mixture of the lecithin and the aromatic compound is prepared and added to the lubricating oil during or followed by the elevated temperature treatment, the most desirable effect on the lubricating oil is obtained.
Although it has been found that polyhydroxy, polyamino, alkylhydroxy and/or aminohydroxy compounds of mono-nuclear or poly-nuclear nature or monoamino or monohydroxy compounds of poly-nuclear nature are most satisfactorily employed, it is also possible to use in combination with or in lieu of such compounds with the lecithin the following compounds:
((1) Monohydroxy-aryl compounds such as phenol and its derivatives;
(12) Monoamino-aryl compounds such as aniline, diphenylamine, acetanilide, acetalaniline, dimethylaniline, amino-diphenyl, benzidine and their derivatives;
Amine condensation products with aldehydes and ketones, such as benzalanilines, formylalphanaphthylamine, butyraldehyde-aniline, aldolaniline and their derivatives;
(d) Nitrogen or oxygen ring compounds, such as furfural, furfuryl alcohol, furoic acid, diphenylguanidine, p-dimethylamino-phenyl-pphenetidylguanidine, pyridine, acridine, triazine, piperidine, quinoline, uric acid, urea, morpholine and their derivatives;
(e) Sulphur compounds, such as thiodiphenylamine, methyl, ethyl, benzyl or phenyl sulphides or mercaptans, phenyl disulphide, benzyl sulphide and their derivatives;
(f) Cyanide compounds such as ethyl, butyl, benzyl or phenyl cyanides and cyanogen and their derivatives;
(g) Aliphatic amines such as dimethylamine, glutamic acid, glycine, triamylamine, n-butyldiamylamine, benzyldiethylamine and their derivatives;
(h) Small amounts of crude pretoleum and preferably a crude petroleum with a naphthenic base, or such fractions or portions of crude petroleum as may be obtained by distillation or solvent extraction which will be high in non-saturated or non-hydrocarbon components, such as, for example, extracts which may be obtained with chlorinated or nitrated aliphatic or aromatic hydrocarbons such as nitrobenzene, chlorinated ethane, chlorinated ethyl ether or low boiling point aliphatic hydrocarbons such as liquefied propane or butane, liquefied sulfur dioxide, phenol, furfural, etc. Extracts may also be made to obtain similar compositions from coal tar or asphaltic or bituminous materials or residues, the preferred compound in such extracts or fractions preferably consisting of normally liquid yet relatively high molecular weight unsaturated ring compounds.
(i) Terpenes or lignin materials such as terpentine, pinene, abietic acid or various crude mixtures containing the same such as tallol, pine oil, rosin oil or their derivatives.
(9') Small amounts of esters or salts in which a metal forms part of the acid radical, for example, such compounds as the phenyl, benzyl, toluyl, cresyl, ethyl, amyl, butyl, propyl and other aryl or alkyl esters of acids including antimony, bismuth, tungsten, chromium, vanadium, thorium, molybdenum, tantalum, columbium, manganese and, less preferably, metals such as iron, lead, tin, or zinc, these metals in all cases preferably all being in a state less than their maximum oxidized state and in ous condition so as to form ites although in some instances the ic acids may be utilized which will form the ates.
Although these compounds preferably have an oxygen atom linking the metal to the carbon of the alkyl or aryl group, it is also possible to use similar compounds in which the carbon is linked directly to the metal atom or in which the intermediate linkage is by way of a sulfur atom rather than an oxygen atom.
Although lecithin is preferred for use in accordance with this invention, it is possible to use cephalin and other similar phosphatides of plant or animal origin. There may also be utilized nerve or brain tissue and meat scrap residues, alcohol and hydrocarbon soluble extracts of crude sugars such as crude cane or beet sugar or their residues such as blackstrap molasses, for combination with the aromatic compound and lubricating oil.
The stabilizing procedures of the present invention are most applicable to non-volatile high molecular weight aliphatic hydrocarbons, and these procedures may also be utilized with high boiling liquid hydrocarbon mixtures derived from other sources than petroleum and even in some instances they may be used with solid high molecular weight hydrocarbon mixtures.
Less preferably, these stabilizing procedures may be employed with non-aliphatic hydrocarbons of high boiling point and still less preferably with high molecular Weight glyceride oils, particularly the triglycerides of high molecular Weight fatty acids having 12 to 36 carbon atoms, which acids may contain if desired one or more double bonds or hydroxy groups.
The invention is not as desirably applicable to hydrocarbons of vegetative origin such as rubber or latex and is not particularly applicable to hydrocarbon compounds of volatile nature or having a boiling point less than about 200 F. to 250 F.
Search Room 252. COMPOSITIONS. Cross Reference Having described my invention, what I claim is:
1. A process of improving lubricating oils consisting substantially of the non-volatile high molecular weight aliphatic hydrocarbons to decrease sludge formation and also to decrease their tendency to cause corrosion of metal surfaces which comprises treating the entire body of such oil with a relatively small amount of a combination of lecithin and p-cresol at an elevated temperature in excess of 350 F.
2. A process of improving lubricating oils consisting substantially of the non-volatile high molecular weight aliphatic hydrocarbons to decrease sludge formation and also to decrease their tendency to cause corrosion of metal surfaces which comprises treating the entire body of such oil with a relatively small amount of a combination of a phosphatide and p-cresol at an eievated temperature in excess of 350 F.
SIDNEY MUSHER.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US359105A US2339797A (en) | 1940-09-30 | 1940-09-30 | Lubricating oil |
| US519379A US2408090A (en) | 1940-09-30 | 1944-01-22 | Lubricating oils |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US359105A US2339797A (en) | 1940-09-30 | 1940-09-30 | Lubricating oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2339797A true US2339797A (en) | 1944-01-25 |
Family
ID=23412321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US359105A Expired - Lifetime US2339797A (en) | 1940-09-30 | 1940-09-30 | Lubricating oil |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2339797A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2429905A (en) * | 1943-09-10 | 1947-10-28 | Sun Oil Co | Lubricant composition |
| US2711374A (en) * | 1951-08-31 | 1955-06-21 | Exxon Research Engineering Co | Corrosion inhibiting composition |
| US2724632A (en) * | 1954-08-09 | 1955-11-22 | Londat Aetz Fabric Co | Cyanoethylated cellulose textiles modified with chromic and periodic acids and process of making same |
| US2966462A (en) * | 1955-11-29 | 1960-12-27 | Gulf Research Development Co | Anti-varnish lubricating composition |
-
1940
- 1940-09-30 US US359105A patent/US2339797A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2429905A (en) * | 1943-09-10 | 1947-10-28 | Sun Oil Co | Lubricant composition |
| US2711374A (en) * | 1951-08-31 | 1955-06-21 | Exxon Research Engineering Co | Corrosion inhibiting composition |
| US2724632A (en) * | 1954-08-09 | 1955-11-22 | Londat Aetz Fabric Co | Cyanoethylated cellulose textiles modified with chromic and periodic acids and process of making same |
| US2966462A (en) * | 1955-11-29 | 1960-12-27 | Gulf Research Development Co | Anti-varnish lubricating composition |
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