US2652367A - Lubricating composition - Google Patents
Lubricating composition Download PDFInfo
- Publication number
- US2652367A US2652367A US177957A US17795750A US2652367A US 2652367 A US2652367 A US 2652367A US 177957 A US177957 A US 177957A US 17795750 A US17795750 A US 17795750A US 2652367 A US2652367 A US 2652367A
- Authority
- US
- United States
- Prior art keywords
- reaction product
- sulfur
- phosphorus
- temperature
- mole
- 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
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- 239000000203 mixture Substances 0.000 title description 37
- 230000001050 lubricating effect Effects 0.000 title description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 91
- 229910052717 sulfur Inorganic materials 0.000 claims description 39
- 239000011593 sulfur Substances 0.000 claims description 39
- -1 SULFUR HALIDE Chemical class 0.000 claims description 37
- 239000000314 lubricant Substances 0.000 claims description 33
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 230000015572 biosynthetic process Effects 0.000 claims description 19
- 230000006866 deterioration Effects 0.000 claims description 17
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 claims description 13
- 239000002480 mineral oil Substances 0.000 claims description 13
- 235000010446 mineral oil Nutrition 0.000 claims description 12
- 229920000768 polyamine Polymers 0.000 claims description 12
- 150000002576 ketones Chemical class 0.000 claims description 9
- 150000003464 sulfur compounds Chemical class 0.000 claims description 9
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 52
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- 239000000047 product Substances 0.000 description 43
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 31
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 30
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- 239000000654 additive Substances 0.000 description 19
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 229910052698 phosphorus Inorganic materials 0.000 description 12
- 239000011574 phosphorus Substances 0.000 description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 238000013019 agitation Methods 0.000 description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 150000003997 cyclic ketones Chemical class 0.000 description 9
- 239000003599 detergent Substances 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 6
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000010687 lubricating oil Substances 0.000 description 5
- WXXNHDGYIVVILR-UHFFFAOYSA-N 2-dodecylbenzaldehyde Chemical compound CCCCCCCCCCCCC1=CC=CC=C1C=O WXXNHDGYIVVILR-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000010685 fatty oil Substances 0.000 description 4
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000010688 mineral lubricating oil Substances 0.000 description 4
- 239000003345 natural gas Substances 0.000 description 4
- 239000012188 paraffin wax Chemical class 0.000 description 4
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 150000001412 amines Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 3
- 239000007777 multifunctional material Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229940100595 phenylacetaldehyde Drugs 0.000 description 3
- 150000003017 phosphorus Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 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
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 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
- 230000000694 effects Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- ZQMPWXFHAUDENN-UHFFFAOYSA-N n,n'-bis(2-methylphenyl)ethane-1,2-diamine Chemical compound CC1=CC=CC=C1NCCNC1=CC=CC=C1C ZQMPWXFHAUDENN-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- DMCJFWXGXUEHFD-UHFFFAOYSA-N pentatriacontan-18-one Chemical compound CCCCCCCCCCCCCCCCCC(=O)CCCCCCCCCCCCCCCCC DMCJFWXGXUEHFD-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000005077 polysulfide Substances 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 150000008117 polysulfides Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 238000006748 scratching Methods 0.000 description 2
- 230000002393 scratching effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- VARQGBHBYZTYLJ-UHFFFAOYSA-N tricosan-12-one Chemical compound CCCCCCCCCCCC(=O)CCCCCCCCCCC VARQGBHBYZTYLJ-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 description 1
- NZGWDASTMWDZIW-MRVPVSSYSA-N (+)-pulegone Chemical compound C[C@@H]1CCC(=C(C)C)C(=O)C1 NZGWDASTMWDZIW-MRVPVSSYSA-N 0.000 description 1
- NDYMQOUYJJXCKJ-UHFFFAOYSA-N (4-fluorophenyl)-morpholin-4-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CCOCC1 NDYMQOUYJJXCKJ-UHFFFAOYSA-N 0.000 description 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- OXVISHZELPRKFQ-UHFFFAOYSA-N 2,2,3-trichlorobutanal Chemical compound CC(Cl)C(Cl)(Cl)C=O OXVISHZELPRKFQ-UHFFFAOYSA-N 0.000 description 1
- WALBTDFSFTVXII-UHFFFAOYSA-N 2,3,4,5,6-pentamethylphenol Chemical compound CC1=C(C)C(C)=C(O)C(C)=C1C WALBTDFSFTVXII-UHFFFAOYSA-N 0.000 description 1
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 1
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 1
- DRRDTKUTHYHEKE-UHFFFAOYSA-N 2,4-dimethyl-6-octylphenol Chemical compound CCCCCCCCC1=CC(C)=CC(C)=C1O DRRDTKUTHYHEKE-UHFFFAOYSA-N 0.000 description 1
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 1
- CJPNOLIZCWDHJK-UHFFFAOYSA-N 2-Pentadecanone Chemical compound CCCCCCCCCCCCCC(C)=O CJPNOLIZCWDHJK-UHFFFAOYSA-N 0.000 description 1
- HVOBSBRYQIYZNY-UHFFFAOYSA-N 2-[2-(2-aminoethylamino)ethylamino]ethanol Chemical compound NCCNCCNCCO HVOBSBRYQIYZNY-UHFFFAOYSA-N 0.000 description 1
- WCWCBLDWXBFHHT-UHFFFAOYSA-N 2-amino-3-benzylphenol Chemical class NC1=C(O)C=CC=C1CC1=CC=CC=C1 WCWCBLDWXBFHHT-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
- AHZRNZSJQJDAQP-UHFFFAOYSA-N 2-cyanooctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C#N)C(O)=O AHZRNZSJQJDAQP-UHFFFAOYSA-N 0.000 description 1
- LGDKJMXNVIFAHE-UHFFFAOYSA-N 2-oxodecanal Chemical compound CCCCCCCCC(=O)C=O LGDKJMXNVIFAHE-UHFFFAOYSA-N 0.000 description 1
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
- YSTPAHQEHQSRJD-UHFFFAOYSA-N 3-Carvomenthenone Chemical compound CC(C)C1CCC(C)=CC1=O YSTPAHQEHQSRJD-UHFFFAOYSA-N 0.000 description 1
- UHRZLJZZZDOHEX-UHFFFAOYSA-N 3-methylheptan-2-one Chemical compound CCCCC(C)C(C)=O UHRZLJZZZDOHEX-UHFFFAOYSA-N 0.000 description 1
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- DGFAPXFUZSHNHQ-UHFFFAOYSA-N 4-methylpent-2-en-3-ol Chemical group CC=C(O)C(C)C DGFAPXFUZSHNHQ-UHFFFAOYSA-N 0.000 description 1
- RLYSXAZAJUMULG-UHFFFAOYSA-N 6-methyl-3-propan-2-ylcyclohex-2-en-1-one Chemical compound CC(C)C1=CC(=O)C(C)CC1 RLYSXAZAJUMULG-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- QNGQIURXCUHNAT-UHFFFAOYSA-N Eucarvone Chemical compound CC1=CC=CC(C)(C)CC1=O QNGQIURXCUHNAT-UHFFFAOYSA-N 0.000 description 1
- OPQCAZJRIRHZQK-UHFFFAOYSA-N Eucarvone Natural products CC1=CC=CCC(C)(C)C1=O OPQCAZJRIRHZQK-UHFFFAOYSA-N 0.000 description 1
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical compound CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
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- VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 1
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- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003470 sulfuric acid monoesters Chemical class 0.000 description 1
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- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Chemical class OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
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- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K11/00—Use of ingredients of unknown constitution, e.g. undefined reaction products
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- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
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- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
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- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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Definitions
- This invention relates to novel reaction products having properties of greatly improving and stabilizing lubricants, such as--mineral lubricating oils, synthetic lubricantsof'hydrocarbon or non-hydrocarbon origin, and the like.
- the invention also pertains to such lubricants containing these reaction products-which act asa multifunctional additive having detergent and antiringsticking properties, aswell as acting as an inhibitor of oxidation and corrosion.
- the invention is directed to products obtained by first reacting an organic carbonyl compound with a polyamine, and treating said reaction product with a sulfurizing (or compound of the sulfur family) phosphorizing or sulfo-phosphorizing agent, such as elemental sulfur, sulfur halides, alkali polysulfides, phosphorus, phosphorus halides and phosphorus oxyhalides, phosphorus sulfides, phosphorus acids, reactive organic phosphorus compounds and the like; the invention is also directed to oleaginous materials, particularly lubricating oils, containing minor amounts of the aforesaid re action products.
- the organic carbonyl compound may be saturated or unsaturated ketones or aldehydes; the following are representative examples:
- Aliphatic ketones such as: acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl n-amyl ketone, dipropyl ketone, ethyl amyl ketone, diisobutyl ketone, diethyl ketone, mesityl oxide and condensation products thereof, 3-methyl-heptanone, methyl vinyl ketone pentanedione, palimitone, laurone, stearone, pentadecanone, etc.
- Aromatic ketones such as: acetophenone, benzophenone, benzyl phenyl ketone, dibenzyl ketone, etc.
- Cyclic ketones such as: isophorone and higher homologues thereof, isophorone bottoms and fraction thereof, cyclobutanone, cyclopentanone, cyclohexanone, methyl cyclohexanone, menthone, camphor, beta decalone, pulegone, piperitone, eucarvone, carvenone, etc.
- ketones such as: diacetyl, acetylacetone, acetonylacetone, cyclohexandione, quinone, benzoyl-acetone, etc.
- Aliphatic aldehydes such as: acetaldehyde, propionaldehyde, butyraldehyde, caproaldehyde, acrolein, croton aldehyde, ethyl butyraldehyde, ethyl propylaldehyde, heptaldehyde, 2-ethy1 hexanal, chloral, butyl chloral, etc.
- Aromatic aldehydes such as: benzaldehyde, paratoluic aldehyde, cinnamaldehyde, salicylaldehyde, naphthaldehyde, vanillin, phenylacetaldehyde, laurylbenzaldehyde, etc.
- the higher molecular weight organic carbonyl compounds particularly the higher molecular weight ketones.
- ketones preferred are the cyclic ketones, such as isophorone bottoms.
- Isophorone bottoms are primarily high molecular weight unsaturated ketones having at least twelve and preferably more than eighteen carbon atoms in the molecule. These products may be obtained by condensation of acetone in a caustic solution under elevated temperature and pressure. Specifically, the product is obtainable by condensing acetone in a 30% to 60% caustic solution at a temperature ranging between about 130 C. and about 170 C., and under a pressure of from about 300 to about 500 pounds per square inch. The resultant product is subjected to distillation to remove distillable ketones and other constituents and impurities.
- the product remaining in the still is preferably purified by filtration, solvent treatment, and comprises crude unsaturated cyclic ketones of high molecular weight, preferably referred to as crude isophorone bottoms.
- crude isophorone bottoms is usually a complex mixture of high molecular weight unsaturated cyclic ketones containing at least twelve and preferably more than eighteen carbon atoms in the molecule.
- These crude isophorone bottoms can be used as such or fractionated and/or chemically treated as disclosed in U. S. Patent 2,489,249.
- the polyamines which can be used to react with the above organic carbonyl compounds in order to form the initial reaction product of this invention are alkylene polyamines such as: ethylene diamine, diethylene triamine, triethylene tetra-amine, tetraethylene pentamine, tetramethyl methylene diamine, propylene diamine, dipropylene triamine, tripropylene tetramine, N-n-dodecyl diethylene triamine, N-octyl ethylene diamine, hydroxyethyl-ethylene diamine, hydroxy isopropyl propylene diamine, hydroxy ethyl diethylene triamine, N-beta-hydroxypropyl propylene diamine, N-n-hexadecyl diethylene triamine, 3-diethyl amino propylamine, 1,3, diamino butane, 1,10 decylene diamine, phenyl ethylene diamine, di-o-tolyl ethylene diamine and the like.
- the initial reaction product of this invention namely, a reaction product obtained by reacting organic carbonyl compounds with polyamines disclosed above is carried out by admixing the reacting materials in a suitable reaction vessel with or without an inert solvent such as benzene, toluene, light hydrocarbons and the like, preferably in the mole ratio of 2 to 6 moles of the carbonyl compound to l to 3 moles of the polyamine.
- the reaction can be carried out at reflux temperature, and generally varies from 50 C. to 250 C., and preferably 80 C. to 180 C., and is continued for a period of time until water formation ceases.
- the water formed is generally removed as it is formed by distillation and any polyamine which is carried over with the water is replaced and the reaction continued until completed.
- the time required to complete the initial reaction varies from 4 to 24 hours.
- the initial reaction product can be freed of unreacted materials, impurities and solvent such as benzene, if used, by heating the reaction product at around 100 C. in a stream of natural gas.
- the final reaction product is obtained by treating an initial reaction product (as described in the preceding paragraph) with a sulfurizing, phosphorizing and/or sulfo-phosphorizing agent preferably in the mole ratio of from 1:1 to 1:8, respectively, and the preferred mole ratio of the reactants is from 1:2 to 1:4.
- sulfurizing, phosphorizing and/or sulfo-phosphorizing agents which can be used to treat the initial reaction product may be included sulfur, H28, SC12, S2C12, sodium tetrasulfide, sodium pentasulfide; POC13, P013, P015, P2S5, P453, selenium, P2Se5 and the like.
- the final reaction is carried out under varying temperature conditions which can range from below zero to above 200 C. and higher.
- the temperature primarily depends on the phosphorizing, sulfurizing and/or sulfo-phosphorizing I agents used to form the final product of this invention. For example, if phosphorus chloride is used the final reaction should be carried out at between 10 C. and zero degrees centigrade, while when sulfur halides are used the tempera,- ture ranges from zero to about C.
- sulfur or sodium polysulfide is used to form the final reaction product, the temperature reaction conditions generally vary between C. and 200 C. and preferably between C. and C.; while if phosphorus sulfides are used the reaction temperature is generally in the range of from 100 C. to C.
- reaction products of this invention can be added to various bases in amounts of from 0.01 to 10% and preferably from about 0.1 to 5%.
- the reaction product was freed from benzene, and small amounts of unchanged ethylene diamine by heating at about 100 C. in a stream of natural gas.
- the product obtained was a dark brown transparent mass, which was non-flowing at room temperature and. on analysis contained 3.0 (8) nitrogen.
- the product was oil soluble and imparted extreme pressure properties to base oil.
- EXAMPLE II A. Initial reaction product of di-isobutyl ketone bottoms with ethylene diamine About two moles of diisobutyl ketone bottoms containing at least eighteen carbon atoms in the molecule and about one mole of ethylene diamine were dispersed in benzene, and the mixture reacted and processed under the same conditions as in Example I(A). The product obtained was a dark brown viscous liquid, which on analysis contains 4.4(4) nitrogen.
- EXAMPLE III A. Initial reaction product of a saturated cyclic ketone fraction containing eighteen carbon atoms and obtained from mesityl oxide condensation with ethylene diamine About two moles of a C18 saturated cyclic ketone (derived from mesityl oxide condensation) and about one mole of ethylene diaminewere reacted under substantially the same conditions as disclosed in Example I(A). The product obtained was a dark brown transparent mass, virtually non-flowing at room temperature and on analysis contained 3.3(3) nitrogen.
- EXAIVIPLE VII A Initial reaction product of topp'ed, crude isophorone bottoms with propylene diamine About two moles of topped, crude isophorone bottoms fraction containing at least eighteen carbon atoms in the molecule and about one mole of propylene diamine were dispersed in benzene and reacted under the condition of Example I(A). The product obtained was a dark brown transparent mass, which was non-flowing at room temperature and on analysis contained over 3% nitrogen.
- EXAMPLE VIII A. Initial reaction product of diisobutyl ketone bottoms with di-o-tolyl ethylene diamine About two moles of diisobutyl ketone bottoms containing at least eighteen carbon atoms in the molecule and about one mole of di-o-toyly ethylene diamine were dispersed in benzene, and the mixture reacted and processed under the same conditions as in Example I(A) The product obtained was a dark brown, viscous liquid, which on analysis contained over 4% nitrogen.
- EXAMZPLE IX A Initial reaction product of benzophenone with ethylene diamine About two moles of benzophenone and about one mole of ethylene diamine were dispersed in benzene, and the entire mixture reacted and processed under the same condition as in Example I(A). The product obtained was a dark brown transparent mass, which was non-flowing at room temperature and on analysis contained over 3% nitrogen.
- EXAMPLE X A Reaction product of butyraldehyde with ethylene diamine About two moles of butyraldehyde and about one mole of ethylene diamine were dispersed in benzene, and the entire mixture reacted under the conditions of Example I(A). The product obtained was a dark brown, transparent mass, which was non-flowing at room temperature and on analysis contained 3% nitrogen.
- the product was oil soluble and possessed extreme pressure properties.
- EXAMPLE XI A Reaction product of lauryl benzaldehyde with ethylene diamine About two moles of lauryl benzaldehyde and about one mole of ethylene diamine were dispersed in benzene, and the entire mixture was heated under conditions of Example I(A). Water was drawn off overhead as lower layer in the benzene-water azeotrope. When water formation ceased, the water layer was titrated with standard acid in order to determine the amount of ethylene diamine that had distilled over. This quantity of the diamine was then added to the reaction vessel, and heating and stirring was resumed until water evolution again ceased. The reaction product was freed from benzene, and small amounts of unchanged ethylene diamine by heating at about 100 C. in a stream of natural gas. The product obtained was non-flowing at room temperature and on analysis contained over 3% nitrogen.
- the product was oil soluble and possessed extreme pressure properties.
- EXAMPLE IHI A. Reaction product of phenylacetaldehyde with ethylene diamine About two moles of phenylacetaldehyde and about one mole of ethylene diamine were dispersed in benzene, and the entire mixture was reacted as in the above initial reactions. The product obtained on analysis contained over 3% nitrogen.
- EXAMPLE XIH A. Reaction product of beneophenone with propylene diamine About two moles of benzophenone and about one mole of propylene diamine were dispersed in benzene, and the entire mixture was reacted as in the above initial reaction. The product obtained on analysis contained over 3% nitrogen.
- the mixture was reacted under constant agitation for about three hours at a temperature of from about to C.
- the product was extracted with a mixture of equal volumes of methyl ethyl ketone and a non-aromatic hydrocarbon having a boiling range of between 164 F. and 233 F.
- the product was filtered and the filtrate evaporated, and found to be oil soluble and possess extreme pressure properties to said oil.
- EXAMPLE XV A Initial reaction product of b enzophenone with ethyiene diamine About two moles of a benzophenone and about one mole of ethylene diamine were reacted under substantially the same conditions as disclosed in Example I(A) The product obtained was a dark brown, transparent mass, virtually non-flowing at room temperature and on analysis contained 3.3(3) nitrogen.
- the final product contained nitrogen and sulfur in the molecule and was oil soluble.
- compositions as indicated in the table below were subjected to Oxygen Absorption and Thrust Bearing Corrosion Tests as described in the National Petroleum News, September 1 1941, pp. R-294 296, and the results as noted are self-explanatory.
- reaction products of this invention inhibits lacquer formation in engines operating under the most adverse conditions.
- reaction products of this invention can be used as valuable constituents of heavy duty oils, motor oils, diesel oils, aviation oils, turbine oil, synthetic oils, dioctyl sebacate, alkylated naphthalene and the like because of their anticorrosion, antioxidation, and antiwear properties.
- reaction products of this invention are useful as anti-oxidants for natural and synthetic rubber and other organic materials which are subject to oxidation deterioration.
- the amount of additive used can be varied over wide limit but generally it is not necessary to use more than by weight of the reaction product, and preferably only between about 0.1 to 2.0% by weight is added to the bases.
- the reaction product of this invention can be combined with other additives in lubricants, such as, blooming agents, pour point depressants or viscosity improvers, extreme pressure agents, antifoaming agents and the like.
- oil-soluble detergents which include oil-soluble salts of various bases with detergent forming acids.
- bases include metal as well as organic bases.
- Metallic bases include those of the alkali metals, Cu, Mg, Ca, Sr, Ba, Zn, Cd, Al, Sn, Pb, Cr, Mn, Fe, Ni, G0, etc.
- Organic bases include various nitrogen bases as primary, secondary, tertiary and quaternary amines.
- detergent forming acids are the various fatty acids of, say, to carbon atoms, wool fat acids, paraffin wax acids (produced by oxidation of paraffin wax) chlorinated fatty acids, rosin acids, aromatic carboxylic acids including aromatic fatty acids, aromatic hydroxy fatty acids, paraffin wax benzoic acids, various alkyl salicylic acids, phthalic acid mono-esters, aromatic keto acids, aromatic ether acids, diphenols as di-(alkyl-phenol) sulfides and disulfides, methylene bis alkylphenols; sulfonic acids such as may be produced by treatment of alkyl aryl hydrocarbons or high boiling petroleum oils with sulfuric acid; sulfuric acid mono-esters; phosphoric, arsonic and antimony acid mono and diesters, including the corresponding thio phosphoric, arsonic and antimony acids; phosphonic and arsonic acids and the like.
- Additional detergents are the alkaline earth phosphate diesters, including the thiophosphate diester; the alkaline earth diphenolates, specifically the calcium and barium salts of diphenol mono and poly sulfides.
- Non-metallic detergents include compounds such as the phosphatides such as lecithin and cephalin, certain fatty oils and rapeseed oils, voltolized fatty or mineral oils and the like.
- An excellent metallic detergent for the present purpose is the calcium salt of oil-soluble petroleum sulfonic acids. This may be present advantageously in the amount of about 0.025% to 0.2% sulfate ash. Also alkaline metal salts of alkyl phenol-aldehyde condensation reaction products are excellent detergents.
- Antioxidants comprise several types, for example, alkyl phenols such as 2,4,6 trimethyl phenol, penta methyl-phenol, 2,4 dimethyl-S-tertiary-butyl phenol, 2,4-dimethyl-6-octyl phenol, 2,6-di-tertiary-butyl-4-methyl-phenol, 2,4,6 tritertiary-butyl phenol and the like; amino phenols as benzyl amino phenols; amines such as dibutylphenylene diamine, diphenyl amine, phenyl-betanaphthylamine, phenyl alpha naphthylamine, dinaphthyl amine.
- alkyl phenols such as 2,4,6 trimethyl phenol, penta methyl-phenol, 2,4 dimethyl-S-tertiary-butyl phenol, 2,4-dimethyl-6-octyl phenol, 2,6-di-tertiary-buty
- Corrosion inhibitors or anti-rusting compounds may also be present such as dicarboxylic acids of 16 and more carbon atoms; alkali metal and alkaline earth salts of sulfonic acids and fatty acids; organic compounds containing an acidic radical in close proximity to a nitrile, nitro or nitroso group (e. g. alpha cyano stearic acid).
- Extreme pressure agents which may be used comprise: esters or phosphorus acids such as triaryl, alkyl hydroxy aryl, or aralkyl phosphates,
- thiophosphates or phosphites and the like neutral aromatic sulfur compounds of relatively high boiling temperatures such as diaryl sulfides, diaryl disulfides, alkyl aryl disulfides, e. g. diphenyl sulfide, diphenol sulfide, dicresol sulfide, dixylenol sulfide, methyl butyl diphenol sulfide, dibenzyl sulfide, corresponding diand tri-sulfides, and the like; sulfurized fatty oils or esters of fatty acids and monohydric alcohols, e. g.
- sulfurized long chain olefins such as may be obtained by dehydrogenation or cracking of wax
- chlorinated hydrocarbons such as chlorinated paraffin, aromatic hydrocarbons, terpenes, mineral lubricating oil, etc.; or chlorinated esters of fatty acids containing the chlorine in position other than alpha position.
- Additional ingredients may comprise oilsoluble urea or thiourea derivatives, e. g. urethanes, allophanates, carbazides, carbazones, etc.; polyisobutylene polymers, unsaturated polymer ized esters of fatty acids and monohydric alcohols and other high molecular weight oil-soluble compounds.
- oilsoluble urea or thiourea derivatives e. g. urethanes, allophanates, carbazides, carbazones, etc.
- polyisobutylene polymers unsaturated polymer ized esters of fatty acids and monohydric alcohols and other high molecular weight oil-soluble compounds.
- the amount of additive used may vary from 0.01 to 2% or higher. However, substantial improvement is obtained by usin amounts ranging from 0.1 to 0.5% in combination with reaction products of this invention.
- novel reaction products of this invention in addition to being excellent lubricating oil improving agents, are potent oxidation inhibitors for fuels, natural and synthetic rubber, wax coating compositions and other organic materials.
- a lubricant comprising a major amount of mineral oil and a minor amount, sufficient to stabilize said lubricant against deterioration, of a reaction product obtained by reacting an organic carbonyl compound selected from the group consisting of ketones and aldehydes with an alkylene polyamine in the mole ratio of 2 to 6:1 to 3, respectively, and at a temperature of from 50 to 250 C. until water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a temperature ranging from below zero degree to about C. and for a period of from 3 to 24 hours.
- a lubricant comprising a major amount of mineral oil and a minor amount, sufficient to stabilize said lubricant against deterioration, of a reaction product obtained by reacting a ketone with an alkylene polyamine in the mole ratio of 2 to 6:1 to 3, respectively, and at a temperature of from 50 to 250 C. until water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a temperature ranging from below zero degree to about 175 C. and for a period of from 3 to 24 hours.
- a lubricant comprising a major amount of mineral oil and a minor amount, sufiicient to stabilize said lubricant against deterioration, of a reaction product obtained by reacting an aldehyde with an alkylene polyamine in the mole ratio of 2 to 6:1 to 3, respectively, and at a temperature of from 50 to 250 C. until water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a temperature ranging from below zero degree to about 175 C. and for a period of from 3 to 24 hours.
- a lubricant comprising a major amount of mineral oil and a minor amount, sufficient to stabilize said oil against deterioration, of a reaction product obtained by reacting a cyclic ketone having at least twelve carbon atoms with alkylene polyamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to 180 C. until water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a temperature ranging from below zero degree to about 175 C. and for a period of from 3 to 24 hours.
- a lubricant comprising a major amount of mineral oil and a minor amount, sufiicient to stabilize said oil against deterioration, of a re action product obtained by reacting a cyclic ketone having at least twelve carbon atoms with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to 180 C. until Water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a temperature ranging from below zero degree to about 175 C and for a period of from 3 to 24 hours.
- a lubricant comprising a major amount of mineral oil and a minor amount, sufficient to stabilize said oil against deterioration, of a reaction product obtained by reacting an isophorone bottoms fraction having at least twelve carbon atoms with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to 180 C. until water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a temperature ranging from below zero degree to about 175 C. and for a period of from 3 to 24 hours.
- a lubricant comprising a major amount of mineral oil and a minor amount, suflicient to stabilize said oil against deterioration, of a reaction product obtained by reacting diisobutyl ketone with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to 180 C. until water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a tem- 14 perature ranging from below zero degree to about 175 C. and for a period of from 3 to 24 hours.
- a lubricant comprising a major amount of mineral oil and a minor amount, sufficient to stabilize said oil against deterioration, of a reaction product obtained by reacting isophorone bottoms fraction having at least twelve carbon atoms with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from to 180 C. until water formation ceases and treating the resulting reaction product with phosphorus sulfide in the mole ratio of from 1:1 to 1:4, respectively, and at a temperature of to 175 C. and for a period of from 3 to 24 hours.
- a lubricant comprising a major amount of mineral oil and a minor amount, sufiicient to stabilize said oil against deterioration, of a reaction product obtained by reacting diisobutyl ketone with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to 180 C. until water formation ceases and treating the resulting reaction product with phosphorus sulfide in the mole ratio of from 1:1 to 1:4, respectively, and at a temperature of 125 to C. and for a period of from 3 to 24 hours.
- a lubricant comprising a major amount of mineral oil and a minor amount, sufiicient to stabilize said oil against deterioration, of a reaction product obtained by reacting isophorone bottoms fraction having at least twelve carbon atoms with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to 180 C. until water formation ceases and treating the resulting reaction product with sulfur in the mole ratio of from 1:1 to 1:4, respectively, and at a temperature of 125 to C. and for a period of from 3 to 24 hours.
- a lubricant comprising a major amount of mineral oil and a minor amount, sufficient to stabilize said oil against deterioration, of a reaction product obtained by reacting isophorone bottoms fraction having at least twelve carbon atoms with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to C. until water formation ceases and treating the resulting reaction product with sulfur halide in the mole ratio of from 1:1 to 1:4, respectively, and at around room temperature and for a period of from 3 to 24 hours.
Description
. mental as an additive in another respect.
Patented Sept. 15, 1953 LUBRICATIN G COMPOSITION David E. Adelson, Berkeley, Calif, assignor to Shell Development Company, San Francisco, Calif., a corporation of Delaware N Drawing. Application August 5, 1950, Serial No. 177,957
13 Claims.
This invention relates to novel reaction products having properties of greatly improving and stabilizing lubricants, such as--mineral lubricating oils, synthetic lubricantsof'hydrocarbon or non-hydrocarbon origin, and the like. The invention also pertains to such lubricants containing these reaction products-which act asa multifunctional additive having detergent and antiringsticking properties, aswell as acting as an inhibitor of oxidation and corrosion.
It is well known thatvarious lubricants, whether doped or undoped; when used in modern engines and machineswhetheroperating under ordinary conditionsor-athigh speeds, elevated temperatures, heavy loads and/or other adverse conditions, tend tooxidizeand to form corrosive bodies and sludges; Someof the deterioration products of lubricants formed during their use are hard, carbonaceous materials which adhere to metal surfaces-and cause scratching and scufiing of movable metal parts and the clogging of valves andpiston rings in engines. In addition, the lubricants are usually incapable of maintaining a continuous lubricating film between movable metal parts, resulting in gradual or rapid wearing away of metal parts. The damage thus caused requires replacement of such parts and/or even the'complete over-hauling of the engines.
In the case of the highest quality non-corrosive lubricating oils, whichhave beenhighly refined for specific uses, or synthetic lubricants developed for specific or special uses, it has been observed that they are generally highly susceptible to oxidation and deterioration;
To improve the lubricating properties of oils and synthetic lubricants, it has become the practice to incorporate into such lubricants, one (and in most cases more than-one) addition agents, which have the effect or property of inhibiting deterioration of such lubricants and to impart to them certain beneficial properties.
The development of numerous additives has been due to the fact that most, if not all, such additives are capable of functioning in substantially only one specific manner. Very few lubricant additives have the ability of improving a lubricant in more than just one respect. Thus, a good anti-oxidant might not be able to inhibit lacquer and varnish formation on piston rods or act as a detergent or corrosion inhibitor. In many cases itis found that an additive possesses very good properties in one respect, but is the cause of harmful. effects and, therefore, detri- This requires the use of "still other additives in order to overcome such defects and to obtain algood stable lubricant; The combination of additives in lubricants wherein each additive exerts its influence withoutinterfering with the-function of other additives is a difficult matter to attain. In most cases additives co-react or interfere with each other. To prevent this, great care must be taken in selecting the additives, mixing them in specific proportions and continuously watching and replacing additives which have stopped functioning or have deteriorated.
It is an object of this invention to improve the lubricating properties of various lubricating bases by the addition thereto of a minor amount of certain multi-functional materials, which material is novel. Another object is to add to compounded or doped lubricants a multi-functional material whereby a synergistic effect is produced, resulting in a product of accentuated and improved properties. Still another object is to add to oleaginous materials, e. g. mineral lubricating oils, synthetic lubricants, and the like, a multi-functional compound which inhibits oxidation and corrosion and helps to prevent the formation of sludge, varnish and lacquer even under adverse operating conditions, and also prevents ring-sticking as well as the sticking of other engine parts due to deterioration of the lubricant. Also, it is an object of this invention to use in oleaginous materials, e. g., in lubricating compositions, a multi-functional material which inhibits wear, scuffing, scratching and other damage to engine parts. Furthermore, it is an object of this invention to provide a novel class of compounds particularly suitable as multi-functional improving and enhancing additives for lubricants. Other objects will appear from the following description of the present invention.
Broadly stated, the invention is directed to products obtained by first reacting an organic carbonyl compound with a polyamine, and treating said reaction product with a sulfurizing (or compound of the sulfur family) phosphorizing or sulfo-phosphorizing agent, such as elemental sulfur, sulfur halides, alkali polysulfides, phosphorus, phosphorus halides and phosphorus oxyhalides, phosphorus sulfides, phosphorus acids, reactive organic phosphorus compounds and the like; the invention is also directed to oleaginous materials, particularly lubricating oils, containing minor amounts of the aforesaid re action products.
The organic carbonyl compound may be saturated or unsaturated ketones or aldehydes; the following are representative examples:
I. Aliphatic ketones, such as: acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl n-amyl ketone, dipropyl ketone, ethyl amyl ketone, diisobutyl ketone, diethyl ketone, mesityl oxide and condensation products thereof, 3-methyl-heptanone, methyl vinyl ketone pentanedione, palimitone, laurone, stearone, pentadecanone, etc.
II. Aromatic ketones, such as: acetophenone, benzophenone, benzyl phenyl ketone, dibenzyl ketone, etc.
III. Cyclic ketones, such as: isophorone and higher homologues thereof, isophorone bottoms and fraction thereof, cyclobutanone, cyclopentanone, cyclohexanone, methyl cyclohexanone, menthone, camphor, beta decalone, pulegone, piperitone, eucarvone, carvenone, etc.
IV. Other types of ketones, such as: diacetyl, acetylacetone, acetonylacetone, cyclohexandione, quinone, benzoyl-acetone, etc.
V. Aliphatic aldehydes, such as: acetaldehyde, propionaldehyde, butyraldehyde, caproaldehyde, acrolein, croton aldehyde, ethyl butyraldehyde, ethyl propylaldehyde, heptaldehyde, 2-ethy1 hexanal, chloral, butyl chloral, etc.
VI. Aromatic aldehydes, such as: benzaldehyde, paratoluic aldehyde, cinnamaldehyde, salicylaldehyde, naphthaldehyde, vanillin, phenylacetaldehyde, laurylbenzaldehyde, etc.
Among the preferred compounds are the higher molecular weight organic carbonyl compounds, particularly the higher molecular weight ketones. Of these ketones, preferred are the cyclic ketones, such as isophorone bottoms.
Isophorone bottoms are primarily high molecular weight unsaturated ketones having at least twelve and preferably more than eighteen carbon atoms in the molecule. These products may be obtained by condensation of acetone in a caustic solution under elevated temperature and pressure. Specifically, the product is obtainable by condensing acetone in a 30% to 60% caustic solution at a temperature ranging between about 130 C. and about 170 C., and under a pressure of from about 300 to about 500 pounds per square inch. The resultant product is subjected to distillation to remove distillable ketones and other constituents and impurities. The product remaining in the still is preferably purified by filtration, solvent treatment, and comprises crude unsaturated cyclic ketones of high molecular weight, preferably referred to as crude isophorone bottoms. The term isophorone bottoms, as referred to herein, is usually a complex mixture of high molecular weight unsaturated cyclic ketones containing at least twelve and preferably more than eighteen carbon atoms in the molecule. These crude isophorone bottoms can be used as such or fractionated and/or chemically treated as disclosed in U. S. Patent 2,489,249.
The polyamines which can be used to react with the above organic carbonyl compounds in order to form the initial reaction product of this invention are alkylene polyamines such as: ethylene diamine, diethylene triamine, triethylene tetra-amine, tetraethylene pentamine, tetramethyl methylene diamine, propylene diamine, dipropylene triamine, tripropylene tetramine, N-n-dodecyl diethylene triamine, N-octyl ethylene diamine, hydroxyethyl-ethylene diamine, hydroxy isopropyl propylene diamine, hydroxy ethyl diethylene triamine, N-beta-hydroxypropyl propylene diamine, N-n-hexadecyl diethylene triamine, 3-diethyl amino propylamine, 1,3, diamino butane, 1,10 decylene diamine, phenyl ethylene diamine, di-o-tolyl ethylene diamine and the like.
The initial reaction product of this invention, namely, a reaction product obtained by reacting organic carbonyl compounds with polyamines disclosed above is carried out by admixing the reacting materials in a suitable reaction vessel with or without an inert solvent such as benzene, toluene, light hydrocarbons and the like, preferably in the mole ratio of 2 to 6 moles of the carbonyl compound to l to 3 moles of the polyamine. The reaction can be carried out at reflux temperature, and generally varies from 50 C. to 250 C., and preferably 80 C. to 180 C., and is continued for a period of time until water formation ceases. The water formed is generally removed as it is formed by distillation and any polyamine which is carried over with the water is replaced and the reaction continued until completed. Generally, the time required to complete the initial reaction varies from 4 to 24 hours. The initial reaction product can be freed of unreacted materials, impurities and solvent such as benzene, if used, by heating the reaction product at around 100 C. in a stream of natural gas.
The final reaction product is obtained by treating an initial reaction product (as described in the preceding paragraph) with a sulfurizing, phosphorizing and/or sulfo-phosphorizing agent preferably in the mole ratio of from 1:1 to 1:8, respectively, and the preferred mole ratio of the reactants is from 1:2 to 1:4.
Among the sulfurizing, phosphorizing and/or sulfo-phosphorizing agents which can be used to treat the initial reaction product may be included sulfur, H28, SC12, S2C12, sodium tetrasulfide, sodium pentasulfide; POC13, P013, P015, P2S5, P453, selenium, P2Se5 and the like.
The final reaction is carried out under varying temperature conditions which can range from below zero to above 200 C. and higher. The temperature primarily depends on the phosphorizing, sulfurizing and/or sulfo-phosphorizing I agents used to form the final product of this invention. For example, if phosphorus chloride is used the final reaction should be carried out at between 10 C. and zero degrees centigrade, while when sulfur halides are used the tempera,- ture ranges from zero to about C. On the other hand, when sulfur or sodium polysulfide is used to form the final reaction product, the temperature reaction conditions generally vary between C. and 200 C. and preferably between C. and C.; while if phosphorus sulfides are used the reaction temperature is generally in the range of from 100 C. to C. In essence the sulfur, phosphorus and/or sulfo-phosphorus materials used to treat the initial reaction product govern the final reaction temperature. Reaction products of this invention can be added to various bases in amounts of from 0.01 to 10% and preferably from about 0.1 to 5%.
To more clearly illustrate the present invention, the following examples are presented.
EXANIPLE I A. Initial reaction product of topped, crude isophorone bottoms with ethylene diamine About two moles of topped, crude isphorone bottoms fraction containing at least eighteen carbon atoms in the molecule and about one mole of ethylene diamine were dispersed in benzene, and the entire mixture was heated at 75-80 C. under a short distillation column bearing a phase separating stillhead. Water was drawn off overhead as lower layer in the benzene-water azeotrope. When water formation ceased, the water layer was titrated with standard acid in order to determine the amount of ethylene diamine that had distilled over. This quantity of the diamine was then added to the reaction vessel, and heating and stirring was resumed until water evolution again ceased. The reaction product was freed from benzene, and small amounts of unchanged ethylene diamine by heating at about 100 C. in a stream of natural gas. The product obtained was a dark brown transparent mass, which was non-flowing at room temperature and. on analysis contained 3.0 (8) nitrogen.
B. Final reaction product obtained by treating I (A) with phosphorus pentasulfide To approximately one mole ofthe above initial reaction product I(A) about two -moles of phosphorus pentasulfide were slowly added, and the mixture was reacted under constant agitation for about three hours at a temperature of from about 125 to 130 C. The product was extracted with a mixture of equal volumes of methyl ethyl ketone and a nonaromatic hydrocarbon having a boiling range of between 164 F. and 233 F. The product was filtered, and the filtrate evaporated. The resultant product was a brittle, dark brown solid, which on analysis contained:
Sulfur, per cent wt 9.8 Phosphorus, per cent wt 7.8 Nitrogen, per cent wt 1.6(7)
The product was oil soluble and imparted extreme pressure properties to base oil.
EXAMPLE II A. Initial reaction product of di-isobutyl ketone bottoms with ethylene diamine About two moles of diisobutyl ketone bottoms containing at least eighteen carbon atoms in the molecule and about one mole of ethylene diamine were dispersed in benzene, and the mixture reacted and processed under the same conditions as in Example I(A). The product obtained was a dark brown viscous liquid, which on analysis contains 4.4(4) nitrogen.
B. Final reaction product obtained by treating II (A) with phosphorus pentasulfide About one mole of the above initial reaction product II(A) and about four moles of P285 were admixed, and the mixture was reacted under constant agitation at a temperature of from about 110 to 150 C. The nitrogen, phosphorus and sulfur-containing reaction product was worked up as in Example 1(3) and was a viscous, brown mass, which analyzed as follows:
Sulfur, per cent Wt 9.7
Phosphorus per cent weight. 7.6 (5) Nitrogen, per cent wt 1.7
EXAMPLE III A. Initial reaction product of a saturated cyclic ketone fraction containing eighteen carbon atoms and obtained from mesityl oxide condensation with ethylene diamine About two moles of a C18 saturated cyclic ketone (derived from mesityl oxide condensation) and about one mole of ethylene diaminewere reacted under substantially the same conditions as disclosed in Example I(A). The product obtained was a dark brown transparent mass, virtually non-flowing at room temperature and on analysis contained 3.3(3) nitrogen.
B. Final reaction product obtained by treating III (A) with sulfur monochloride To approximately two moles of the above reaction product, about one mole of-sulfur monochloride was added dropwise at ice temperature, and the mixture was stirred vigorously and warmed slowly to room temperature over a period of about twenty-four hours. The reaction prod-- uct was then heated for about three hours on a steam bath and thereafter separately solvent treated, first with a non-aromatic hydrocarbon and then with methyl ethyl ketone as in Example I. The non-aromatic hydrocarbon portion was a dark brown viscous mass, and on analysis contained:
Carbon, per cent wt. -aa- 68.8(9) Hydrogen, per cent wt 919(7) Nitrogen, per cent wt. 2.1(9') Chlorine, per cent wt. 5.2(2) Sulfur, per cent wt. 918(5) Oxygen, per cent wt. (by diiference) 3.8(8)
While the methyl ethyl ketone portion on analysis contained:
Carbon, per cent wt. 6014(7) Hydrogen, per cent wt. 8.5(0) Nitrogen, per cent wt 314(1) Chlorine, per cent wt. 7.7(9)
Sulfur, per cent wt. 13.5 Oxygen, per cent Wt. (by difference) 6.3(3)
Nitrogen, per cent wt. 2.7 (6) Chlorine, per cent wt. 424(1) Sulfur, per cent wt. 23.9
while the insoluble portion of the reaction product was a black, brittle-solid, which on analysis contained:
Nitrogen, per cent wt.
EXAMPLE V About one mole of the initial reaction product of Example I(A) was admixed with two moles of flower of sulfur, .and themi xture was heated for about three hourswith vigorous agitation at "-l70 C. The reaction product was solvent treated with a light hydrocarbon,.filtered and on removing the solvent a dark brown viscous material, which was nonfiowing at room temperature, was obtained, which onanalysis contained:
Nitrogen, per cent wt 2.0(6) Sulfur, per cent wt 7:3(2)
EXAMPLE VI About one mole of the initial reaction product of Example III(A) and four moles of flower of sulfur were admixed'andreacted under the same conditions as described in-Example V. The solvent-treated product was a dark brown, semisolid mass, which-on analysis-contained:
EXAIVIPLE VII A. Initial reaction product of topp'ed, crude isophorone bottoms with propylene diamine About two moles of topped, crude isophorone bottoms fraction containing at least eighteen carbon atoms in the molecule and about one mole of propylene diamine were dispersed in benzene and reacted under the condition of Example I(A). The product obtained was a dark brown transparent mass, which was non-flowing at room temperature and on analysis contained over 3% nitrogen.
B. Final reaction roduct obtained by treated VII (A) with phosphorus pentasulfide To approximately one mole of the above initial reaction product VII(A) about two moles of phosphorus pentasulfide was slowly added, and the-mixture was reacted under constant agitation for about three hours at atemperature of from about 125 to 130 C. The product was extracted with a mixture of equal volumes of methyl ethyl ketone and a non-aromatic hydrocarbon hav ing a boiling range of between 164 F. and 233 F. The product was filtered and the filtrate evaporated. The resultant product on analysis contained sulfur, phosphorus and nitrogen in the molecule and was oil soluble.
EXAMPLE VIII A. Initial reaction product of diisobutyl ketone bottoms with di-o-tolyl ethylene diamine About two moles of diisobutyl ketone bottoms containing at least eighteen carbon atoms in the molecule and about one mole of di-o-toyly ethylene diamine were dispersed in benzene, and the mixture reacted and processed under the same conditions as in Example I(A) The product obtained was a dark brown, viscous liquid, which on analysis contained over 4% nitrogen.
B. Final reaction product obtained by treating VIII (A) with phosphorus pentasulflde About one mole of the above initial reaction product VIII(A) and about four moles of P2S5 were admixed and the mixture was reacted under constant agitation at a temperature of from about 110 to 150 C. The nitrogen phosphorusand sulfur-containing reaction product was worked up as in Example 1(3) and was a viscous, brown mass, which on analysis contained sulfur, phosphorus and nitrogen in the molecule.
EXAMZPLE IX A. Initial reaction product of benzophenone with ethylene diamine About two moles of benzophenone and about one mole of ethylene diamine were dispersed in benzene, and the entire mixture reacted and processed under the same condition as in Example I(A). The product obtained was a dark brown transparent mass, which was non-flowing at room temperature and on analysis contained over 3% nitrogen.
B. Final reaction product obtained by treating IX (A) with phosphorus pentasulfide To approximately one mole of the above initial reaction product IX(A) about two moles of phosphorus pentasulfide were slowly added, and the mixture was reacted under constant agitation for about three hours at a temperature of from about 125 to 150 C. The product was extracted with a mixture of equal volumes of methyl ethyl ke- 8 toneand a non-aromatic hydrocarbon having a boiling range of between 164 F. and 233 F. The product was filtered, and the filtrate evaporated. The resultant product contained sulfur, phosphorus and nitrogen in the molecule and was oil soluble and possessed extreme pressure properties.
EXAMPLE X A. Reaction product of butyraldehyde with ethylene diamine About two moles of butyraldehyde and about one mole of ethylene diamine were dispersed in benzene, and the entire mixture reacted under the conditions of Example I(A). The product obtained was a dark brown, transparent mass, which was non-flowing at room temperature and on analysis contained 3% nitrogen.
B. Final reaction product obtained by treating X (A) with phosphorus pentasulfide To approximately one mole of the above initial reaction product X(A) about two moles of phosphorus pentasulfide were slowly added, and the mixture was reacted under constant agitation for about three hours at a temperature of from about to C. The product was extracted with a mixture of equal volumes of methyl ethyl ketone and a non-aromatic hydrocarbon having a boiling range of between 164 F. and 233 F. The product was filtered and the filtrate evaporated.
The product was oil soluble and possessed extreme pressure properties.
EXAMPLE XI A. Reaction product of lauryl benzaldehyde with ethylene diamine About two moles of lauryl benzaldehyde and about one mole of ethylene diamine were dispersed in benzene, and the entire mixture was heated under conditions of Example I(A). Water was drawn off overhead as lower layer in the benzene-water azeotrope. When water formation ceased, the water layer was titrated with standard acid in order to determine the amount of ethylene diamine that had distilled over. This quantity of the diamine was then added to the reaction vessel, and heating and stirring was resumed until water evolution again ceased. The reaction product was freed from benzene, and small amounts of unchanged ethylene diamine by heating at about 100 C. in a stream of natural gas. The product obtained was non-flowing at room temperature and on analysis contained over 3% nitrogen.
B. Final reaction product obtained by treating XJ (A) with phosphorus pentasulfide To approximately one mole of the above initial reaction product XI(A) about two moles of phosphorus pentasulfide were slowly added, and the mixture was reacted under constant agitation for about three hours at a temperature of from about 125 to C. The product was extracted with a mixture of equal volumes of methyl ethyl ketone and a non-aromatic hydrocarbon having a boiling range of between 164 F. and 233 F. The product was filtered and the filtrate evaporated.
The product was oil soluble and possessed extreme pressure properties.
EXAMPLE IHI A.. Reaction product of phenylacetaldehyde with ethylene diamine About two moles of phenylacetaldehyde and about one mole of ethylene diamine were dispersed in benzene, and the entire mixture was reacted as in the above initial reactions. The product obtained on analysis contained over 3% nitrogen.
B. Final reaction product obtained by treating XII (A) with phosphorus pentasulfide To approximately one mole of the above initial reaction product XII(A) about two moles of phosphorus pentasulfide were slowly added, and the mixture was reacted under constant agitation for about three hours at a temperature of from about 125 to 150 C. The product was extracted with a mixture of equal volumes of methyl ethyl ketone and a non-aromatic hydrocarbon having a boiling range of between 164 F. and 233 F. The product was filtered and the filtrate evaporated and found to be oil soluble and DOS-7 sessed extreme pressure properties.
EXAMPLE XIH A. Reaction product of beneophenone with propylene diamine About two moles of benzophenone and about one mole of propylene diamine were dispersed in benzene, and the entire mixture was reacted as in the above initial reaction. The product obtained on analysis contained over 3% nitrogen.
B. Final reaction product obtained by treating XIII (A) with phosphorus pentasulfide To approximately one mole of the above initial reaction product XIII(A) about two moles of phosphorus pentasulfide were slowly added, and the mixture was reacted under constant agitation for about three hours at a temperature of from about 125 to 150 C. The product was extracted EXAMPLE XIV A. Reaction product of Zauryl benzaldehyde with cliethylene triamine About two moles of lauryl benzaldehyde fraction containing at least eighteen carbon atoms in the molecule and about one mole of diethylene triamine were dispersed in benzene, and the entire mixture was heated at 75-80 C. under a short distillation column bearing a phase-separating stillhead. Water was drawn off overhead as lower layer in the benzene-water azeotrope. When water formation ceased, the water layer was titrated with standard acid in order to determine the amount of diethylene triamine that had distilled over. This quantity of the triamine was then added to the reaction vessel, and heating and stirring was resumed until water evolution again ceased. The reaction product was freed from benzene, and small amounts of unchanged diethylene triamine by heating at about 100 C. in a stream of natural gas. 'The product obtained was a dark brown, transparent mass, which was non-flowing at room temperature and on analysis contained over 3% nitrogen.
13. Final reaction product obtained by treating XIV(A) with phosphorus pentasulfide To approximately one mole of the above initial reaction product XIV(A) about two moles of phosphorus pentasulfide were slowly added, and
the mixture was reacted under constant agitation for about three hours at a temperature of from about to C. The product was extracted with a mixture of equal volumes of methyl ethyl ketone and a non-aromatic hydrocarbon having a boiling range of between 164 F. and 233 F. The product was filtered and the filtrate evaporated, and found to be oil soluble and possess extreme pressure properties to said oil.
EXAMPLE XV A. Initial reaction product of b enzophenone with ethyiene diamine About two moles of a benzophenone and about one mole of ethylene diamine were reacted under substantially the same conditions as disclosed in Example I(A) The product obtained was a dark brown, transparent mass, virtually non-flowing at room temperature and on analysis contained 3.3(3) nitrogen.
B. Final reaction product obtained by treating XT/(A) with sulfur monochloride To approximately two moles of the above reaction product about one mole "of sulfur monochloride was added dropwise at ice temperature, and the mixture was stirred vigorously and warmed slowly to room temperature over a period of about twenty-four hours. The reaction product was then heated for about three hours on a steam bath, and thereafter separately solventtreated, first with a non-aromatic hydrocarbon and then with methyl ethyl ketone as in Example I.
1 The final product contained nitrogen and sulfur in the molecule and was oil soluble.
To illustrate the pronounced improvement obtained in lubricating compositions by the addition of small amounts of reaction products of this invention, compositions as indicated in the table below were subjected to Oxygen Absorption and Thrust Bearing Corrosion Tests as described in the National Petroleum News, September 1 1941, pp. R-294 296, and the results as noted are self-explanatory.
Oxidation TestRefined, undoped. lubricating oil, SUS at 210 F. of 64-67 was employed, oxidation atO.-Catalyst: l cm. Cu/g. oil
Thrust Bearing CorrosionEstimated approximate critical corrosion Composition In addition to the above properties the addition of reaction products of this invention to mineral lubricating oils inhibits lacquer formation in engines operating under the most adverse conditions. Also reaction products of this invention can be used as valuable constituents of heavy duty oils, motor oils, diesel oils, aviation oils, turbine oil, synthetic oils, dioctyl sebacate, alkylated naphthalene and the like because of their anticorrosion, antioxidation, and antiwear properties. Besides their utility as lubricating oil additives, reaction products of this invention are useful as anti-oxidants for natural and synthetic rubber and other organic materials which are subject to oxidation deterioration. The amount of additive used can be varied over wide limit but generally it is not necessary to use more than by weight of the reaction product, and preferably only between about 0.1 to 2.0% by weight is added to the bases.
Because of its synergistic effect the reaction product of this invention can be combined with other additives in lubricants, such as, blooming agents, pour point depressants or viscosity improvers, extreme pressure agents, antifoaming agents and the like. Among the specific additives which can be used are oil-soluble detergents which include oil-soluble salts of various bases with detergent forming acids. Such bases include metal as well as organic bases. Metallic bases include those of the alkali metals, Cu, Mg, Ca, Sr, Ba, Zn, Cd, Al, Sn, Pb, Cr, Mn, Fe, Ni, G0, etc. Organic bases include various nitrogen bases as primary, secondary, tertiary and quaternary amines.
Examples of detergent forming acids are the various fatty acids of, say, to carbon atoms, wool fat acids, paraffin wax acids (produced by oxidation of paraffin wax) chlorinated fatty acids, rosin acids, aromatic carboxylic acids including aromatic fatty acids, aromatic hydroxy fatty acids, paraffin wax benzoic acids, various alkyl salicylic acids, phthalic acid mono-esters, aromatic keto acids, aromatic ether acids, diphenols as di-(alkyl-phenol) sulfides and disulfides, methylene bis alkylphenols; sulfonic acids such as may be produced by treatment of alkyl aryl hydrocarbons or high boiling petroleum oils with sulfuric acid; sulfuric acid mono-esters; phosphoric, arsonic and antimony acid mono and diesters, including the corresponding thio phosphoric, arsonic and antimony acids; phosphonic and arsonic acids and the like.
Additional detergents are the alkaline earth phosphate diesters, including the thiophosphate diester; the alkaline earth diphenolates, specifically the calcium and barium salts of diphenol mono and poly sulfides.
Non-metallic detergents include compounds such as the phosphatides such as lecithin and cephalin, certain fatty oils and rapeseed oils, voltolized fatty or mineral oils and the like.
An excellent metallic detergent for the present purpose is the calcium salt of oil-soluble petroleum sulfonic acids. This may be present advantageously in the amount of about 0.025% to 0.2% sulfate ash. Also alkaline metal salts of alkyl phenol-aldehyde condensation reaction products are excellent detergents.
Antioxidants comprise several types, for example, alkyl phenols such as 2,4,6 trimethyl phenol, penta methyl-phenol, 2,4 dimethyl-S-tertiary-butyl phenol, 2,4-dimethyl-6-octyl phenol, 2,6-di-tertiary-butyl-4-methyl-phenol, 2,4,6 tritertiary-butyl phenol and the like; amino phenols as benzyl amino phenols; amines such as dibutylphenylene diamine, diphenyl amine, phenyl-betanaphthylamine, phenyl alpha naphthylamine, dinaphthyl amine.
Corrosion inhibitors or anti-rusting compounds may also be present such as dicarboxylic acids of 16 and more carbon atoms; alkali metal and alkaline earth salts of sulfonic acids and fatty acids; organic compounds containing an acidic radical in close proximity to a nitrile, nitro or nitroso group (e. g. alpha cyano stearic acid).
Extreme pressure agents which may be used comprise: esters or phosphorus acids such as triaryl, alkyl hydroxy aryl, or aralkyl phosphates,
thiophosphates or phosphites and the like; neutral aromatic sulfur compounds of relatively high boiling temperatures such as diaryl sulfides, diaryl disulfides, alkyl aryl disulfides, e. g. diphenyl sulfide, diphenol sulfide, dicresol sulfide, dixylenol sulfide, methyl butyl diphenol sulfide, dibenzyl sulfide, corresponding diand tri-sulfides, and the like; sulfurized fatty oils or esters of fatty acids and monohydric alcohols, e. g. sperm oil, jojoba oil, etc.; in which the sulfur is strongly bonded; sulfurized long chain olefins such as may be obtained by dehydrogenation or cracking of wax; sulfurized phosphorized fatty oils or acids, phosphorus acid esters having sulfurized organic radicals, such as esters of phosphoric or phosphorus acids with sulfurized hydroxy fatty acids; chlorinated hydrocarbons, such as chlorinated paraffin, aromatic hydrocarbons, terpenes, mineral lubricating oil, etc.; or chlorinated esters of fatty acids containing the chlorine in position other than alpha position.
Additional ingredients may comprise oilsoluble urea or thiourea derivatives, e. g. urethanes, allophanates, carbazides, carbazones, etc.; polyisobutylene polymers, unsaturated polymer ized esters of fatty acids and monohydric alcohols and other high molecular weight oil-soluble compounds.
Depending upon the additive used and conditions under which it is used, the amount of additive used may vary from 0.01 to 2% or higher. However, substantial improvement is obtained by usin amounts ranging from 0.1 to 0.5% in combination with reaction products of this invention.
The novel reaction products of this invention, in addition to being excellent lubricating oil improving agents, are potent oxidation inhibitors for fuels, natural and synthetic rubber, wax coating compositions and other organic materials.
It is to be understood that while the features of the invention have been described and illustrated in connection with certain specific examples, the invention, however, is not to be limited thereto or otherwise restricted, except by the prior art and the scope of the appended claims.
The invention claimed is:
1. A lubricant comprising a major amount of mineral oil and a minor amount, sufficient to stabilize said lubricant against deterioration, of a reaction product obtained by reacting an organic carbonyl compound selected from the group consisting of ketones and aldehydes with an alkylene polyamine in the mole ratio of 2 to 6:1 to 3, respectively, and at a temperature of from 50 to 250 C. until water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a temperature ranging from below zero degree to about C. and for a period of from 3 to 24 hours.
2. A lubricant comprising a major amount of mineral oil and a minor amount, sufficient to stabilize said lubricant against deterioration, of a reaction product obtained by reacting a ketone with an alkylene polyamine in the mole ratio of 2 to 6:1 to 3, respectively, and at a temperature of from 50 to 250 C. until water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a temperature ranging from below zero degree to about 175 C. and for a period of from 3 to 24 hours.
3. A lubricant comprising a major amount of mineral oil and a minor amount, sufiicient to stabilize said lubricant against deterioration, of a reaction product obtained by reacting an aldehyde with an alkylene polyamine in the mole ratio of 2 to 6:1 to 3, respectively, and at a temperature of from 50 to 250 C. until water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a temperature ranging from below zero degree to about 175 C. and for a period of from 3 to 24 hours.
4. A lubricant comprising a major amount of mineral oil and a minor amount, sufficient to stabilize said oil against deterioration, of a reaction product obtained by reacting a cyclic ketone having at least twelve carbon atoms with alkylene polyamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to 180 C. until water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a temperature ranging from below zero degree to about 175 C. and for a period of from 3 to 24 hours.
5. A lubricant comprising a major amount of mineral oil and a minor amount, sufiicient to stabilize said oil against deterioration, of a re action product obtained by reacting a cyclic ketone having at least twelve carbon atoms with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to 180 C. until Water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a temperature ranging from below zero degree to about 175 C and for a period of from 3 to 24 hours.
6. A lubricant comprising a major amount of mineral oil and a minor amount, sufficient to stabilize said oil against deterioration, of a reaction product obtained by reacting an isophorone bottoms fraction having at least twelve carbon atoms with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to 180 C. until water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a temperature ranging from below zero degree to about 175 C. and for a period of from 3 to 24 hours.
7. A lubricant comprising a major amount of mineral oil and a minor amount, suflicient to stabilize said oil against deterioration, of a reaction product obtained by reacting diisobutyl ketone with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to 180 C. until water formation ceases and treating the resulting reaction product with an inorganic carbon-free sulfur compound selected from the group consisting of phosphorus sulfide, sulfur halide, and sulfur in the mole ratio of from 1:1 to 1:8, respectively, at a tem- 14 perature ranging from below zero degree to about 175 C. and for a period of from 3 to 24 hours.
8. A lubricant comprising a major amount of mineral oil and a minor amount, sufficient to stabilize said oil against deterioration, of a reaction product obtained by reacting isophorone bottoms fraction having at least twelve carbon atoms with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from to 180 C. until water formation ceases and treating the resulting reaction product with phosphorus sulfide in the mole ratio of from 1:1 to 1:4, respectively, and at a temperature of to 175 C. and for a period of from 3 to 24 hours.
9. A lubricant comprising a major amount of mineral oil and a minor amount, sufiicient to stabilize said oil against deterioration, of a reaction product obtained by reacting diisobutyl ketone with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to 180 C. until water formation ceases and treating the resulting reaction product with phosphorus sulfide in the mole ratio of from 1:1 to 1:4, respectively, and at a temperature of 125 to C. and for a period of from 3 to 24 hours.
10. A lubricant comprising a major amount of mineral oil and a minor amount, sufiicient to stabilize said oil against deterioration, of a reaction product obtained by reacting isophorone bottoms fraction having at least twelve carbon atoms with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to 180 C. until water formation ceases and treating the resulting reaction product with sulfur in the mole ratio of from 1:1 to 1:4, respectively, and at a temperature of 125 to C. and for a period of from 3 to 24 hours.
11. A lubricant comprising a major amount of mineral oil and a minor amount, sufficient to stabilize said oil against deterioration, of a reaction product obtained by reacting isophorone bottoms fraction having at least twelve carbon atoms with ethylene diamine in the mole ratio of 2 to 6:1 to 3, respectively, at a temperature of from 80 to C. until water formation ceases and treating the resulting reaction product with sulfur halide in the mole ratio of from 1:1 to 1:4, respectively, and at around room temperature and for a period of from 3 to 24 hours.
12. A lubricating composition of claim 4 wherein the cyclic ketone is isophorone bottoms having at least 12 carbon atoms and the alkylene polyamine is propylene diamine and the carbon-free sulfur compound is phosphorus pentasulfide.
13. A lubricating composition of claim 8 wherein the reactants, isophorone bottoms having at least twelve carbon atoms and ethylene diamine, are in the mole ratio of 2:1, respectively, and the phosphorus sulfide is phosphorus pentasulfide.
DAVID E. ADELSON".
References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,006,710 Downing July 2, 1935 2,243,172 Sibley May 27, 1941 2,403,474 Bartleson et a1 July 9, 1946 2,483,736 Otto et a1. Oct. 4, 1949 2,495,478 Redman Jan. 24, 1950 2,516,119 Hersh July 25, 1950
Claims (1)
1. A LUBRICANT COMPRISING A MAJOR AMOUNT OF MINERAL OIL AND A MINOR AMOUNT, SUFFICIENT TO STABILIZE SAID LUBRICANT AGAINST DETERIORATION, OF A REACTION PRODUCT OBTAINED BY REACTING AN ORGANIC CARBONYL COMPOUND SELECTED FROM THE GROUP CONSISTING OF KETONES AND ALDEHYDES WITH AN ALKYLENE POLYAMINE IN THE MOLE RATIO OF 2 TO 6:1 TO 3, RESPECTIVELY, AND AT A TEMPERATURE OF FROM 50 TO 250* C. UNTIL WATER FORMATION CEASES AND TREATING THE RESULTING REACTION PRODUCT WITH AN INORGANIC CARBON-FREE SULFUR COMPOUND SELECTED FROM THE GROUP CONSISTING OR PHOSPHORUS SULFIDE, SULFUR HALIDE, AND SULFUR IN THE MOLE RATIO OF FROM 1:1 TO 1:8, RESPECTIVELY, AT A TEMPERATURE RANGING FROM BELOW ZERO DEGREE TO ABOUT 175* C. AND FOR A PERIOD OF FROM 3 TO 24 HOURS.
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US177957A US2652367A (en) | 1950-08-05 | 1950-08-05 | Lubricating composition |
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US177957A US2652367A (en) | 1950-08-05 | 1950-08-05 | Lubricating composition |
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Cited By (15)
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US2760957A (en) * | 1953-06-01 | 1956-08-28 | Shell Dev | Phosphorus and/or sulfur-containing reaction products of carbonyl compounds and polyamines |
US2954344A (en) * | 1957-12-11 | 1960-09-27 | Exxon Research Engineering Co | Heavy duty lubricating oil |
US3097170A (en) * | 1962-07-05 | 1963-07-09 | Sinclair Research Inc | Phosphosulfurized material and extreme pressure lubricant containing the same |
US3161612A (en) * | 1959-04-15 | 1964-12-15 | Bayer Ag | Alkylated amino phenols protecting rubber goods against ozone |
US3420800A (en) * | 1963-02-04 | 1969-01-07 | Ici Ltd | Polymeric materials produced by interacting polyisocyanate and water in the presence of polyaldimine or polyketimine |
US3461100A (en) * | 1964-07-02 | 1969-08-12 | Tracor | Condensation products of aldehydes or ketones with diamines and monoamines |
US3506613A (en) * | 1969-01-15 | 1970-04-14 | Owens Illinois Inc | Novel polymers prepared from aliphatic diketones and aliphatic diamines |
US4025451A (en) * | 1973-09-14 | 1977-05-24 | Ethyl Corporation | Sulfurized mannich bases as lubricating oil dispersant |
US4028414A (en) * | 1969-01-02 | 1977-06-07 | Atlantic Richfield Company | Process, products and composition |
US4064044A (en) * | 1971-07-06 | 1977-12-20 | Petrolite Corporation | Process for chelating and inhibiting scale in aqueous systems |
US4169859A (en) * | 1969-01-02 | 1979-10-02 | Atlantic Richfield Company | Process, products and composition |
US4253978A (en) * | 1979-10-01 | 1981-03-03 | Mobil Oil Corporation | Phosphorus-containing compounds and lubricants containing same |
US4317738A (en) * | 1980-10-10 | 1982-03-02 | Standard Oil Company (Indiana) | Dispersants and dispersant viscosity modifiers from oxidized-sulfurized olefins |
US4317739A (en) * | 1980-10-10 | 1982-03-02 | Standard Oil Company (Indiana) | Aminated sulfurized olefin funtionalized with a boron compound and formaldehyde |
US20070135615A1 (en) * | 2005-12-12 | 2007-06-14 | Kao Corporation | Polyester for toner |
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Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2760957A (en) * | 1953-06-01 | 1956-08-28 | Shell Dev | Phosphorus and/or sulfur-containing reaction products of carbonyl compounds and polyamines |
US2954344A (en) * | 1957-12-11 | 1960-09-27 | Exxon Research Engineering Co | Heavy duty lubricating oil |
US3161612A (en) * | 1959-04-15 | 1964-12-15 | Bayer Ag | Alkylated amino phenols protecting rubber goods against ozone |
US3097170A (en) * | 1962-07-05 | 1963-07-09 | Sinclair Research Inc | Phosphosulfurized material and extreme pressure lubricant containing the same |
US3420800A (en) * | 1963-02-04 | 1969-01-07 | Ici Ltd | Polymeric materials produced by interacting polyisocyanate and water in the presence of polyaldimine or polyketimine |
US3461100A (en) * | 1964-07-02 | 1969-08-12 | Tracor | Condensation products of aldehydes or ketones with diamines and monoamines |
US4028414A (en) * | 1969-01-02 | 1977-06-07 | Atlantic Richfield Company | Process, products and composition |
US4169859A (en) * | 1969-01-02 | 1979-10-02 | Atlantic Richfield Company | Process, products and composition |
US3506613A (en) * | 1969-01-15 | 1970-04-14 | Owens Illinois Inc | Novel polymers prepared from aliphatic diketones and aliphatic diamines |
US4064044A (en) * | 1971-07-06 | 1977-12-20 | Petrolite Corporation | Process for chelating and inhibiting scale in aqueous systems |
US4025451A (en) * | 1973-09-14 | 1977-05-24 | Ethyl Corporation | Sulfurized mannich bases as lubricating oil dispersant |
US4253978A (en) * | 1979-10-01 | 1981-03-03 | Mobil Oil Corporation | Phosphorus-containing compounds and lubricants containing same |
US4317738A (en) * | 1980-10-10 | 1982-03-02 | Standard Oil Company (Indiana) | Dispersants and dispersant viscosity modifiers from oxidized-sulfurized olefins |
US4317739A (en) * | 1980-10-10 | 1982-03-02 | Standard Oil Company (Indiana) | Aminated sulfurized olefin funtionalized with a boron compound and formaldehyde |
US20070135615A1 (en) * | 2005-12-12 | 2007-06-14 | Kao Corporation | Polyester for toner |
US7528218B2 (en) * | 2005-12-12 | 2009-05-05 | Kao Corporation | Polyester for toner |
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