US2796401A - Complex formal lubricating composition - Google Patents
Complex formal lubricating composition Download PDFInfo
- Publication number
- US2796401A US2796401A US323338A US32333852A US2796401A US 2796401 A US2796401 A US 2796401A US 323338 A US323338 A US 323338A US 32333852 A US32333852 A US 32333852A US 2796401 A US2796401 A US 2796401A
- Authority
- US
- United States
- Prior art keywords
- alcohol
- glycol
- complex
- formal
- viscosity
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title description 34
- 230000001050 lubricating effect Effects 0.000 title description 16
- 239000000314 lubricant Substances 0.000 claims description 26
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 41
- 235000019441 ethanol Nutrition 0.000 description 34
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 24
- -1 2-ethyl-1-butanol 2-ethyl-1-hexanol Chemical compound 0.000 description 21
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 150000001298 alcohols Chemical class 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000004435 Oxo alcohol Substances 0.000 description 10
- 235000019256 formaldehyde Nutrition 0.000 description 10
- 239000004519 grease Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 238000002485 combustion reaction Methods 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 8
- 230000001476 alcoholic effect Effects 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000002334 glycols Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 150000002440 hydroxy compounds Chemical class 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 150000001721 carbon Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 4
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OLQJQHSAWMFDJE-UHFFFAOYSA-N 2-(hydroxymethyl)-2-nitropropane-1,3-diol Chemical compound OCC(CO)(CO)[N+]([O-])=O OLQJQHSAWMFDJE-UHFFFAOYSA-N 0.000 description 3
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000003893 lactate salts Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920001748 polybutylene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000010689 synthetic lubricating oil Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- ZENOXNGFMSCLLL-UHFFFAOYSA-N vanillyl alcohol Chemical compound COC1=CC(CO)=CC=C1O ZENOXNGFMSCLLL-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- AQIUDFSBFDYTGN-UHFFFAOYSA-N 2-aminoethanol;2-aminopropan-1-ol Chemical compound NCCO.CC(N)CO AQIUDFSBFDYTGN-UHFFFAOYSA-N 0.000 description 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
- MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical compound OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- DYPJJAAKPQKWTM-UHFFFAOYSA-N 2-chloropropane-1,3-diol Chemical compound OCC(Cl)CO DYPJJAAKPQKWTM-UHFFFAOYSA-N 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- AKXKFZDCRYJKTF-UHFFFAOYSA-N 3-Hydroxypropionaldehyde Chemical compound OCCC=O AKXKFZDCRYJKTF-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
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- 101100492584 Caenorhabditis elegans ast-1 gene Proteins 0.000 description 1
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- 101100021869 Drosophila melanogaster Lrch gene Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
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- 241000282326 Felis catus Species 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000007869 Guerbet synthesis reaction Methods 0.000 description 1
- SHBUUTHKGIVMJT-UHFFFAOYSA-N Hydroxystearate Chemical class CCCCCCCCCCCCCCCCCC(=O)OO SHBUUTHKGIVMJT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
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- QDFXSEXGAIWDFP-UHFFFAOYSA-N [N+](=O)([O-])C(CO)CC.[N+](=O)([O-])C(CO)C Chemical compound [N+](=O)([O-])C(CO)CC.[N+](=O)([O-])C(CO)C QDFXSEXGAIWDFP-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
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- 150000001299 aldehydes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
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- 238000006555 catalytic reaction Methods 0.000 description 1
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- 229910017052 cobalt Inorganic materials 0.000 description 1
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- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
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- 239000000539 dimer Substances 0.000 description 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- LQZALHTWCLNAIE-UHFFFAOYSA-N ethanol;morpholine Chemical compound CCO.C1COCCN1 LQZALHTWCLNAIE-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000013531 gin Nutrition 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
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- 230000007775 late Effects 0.000 description 1
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- 229920000098 polyolefin Polymers 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
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Classifications
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- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] containing hydroxyl groups; Alkoxylated derivatives
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/20—Containing nitrogen-to-oxygen bonds
- C10M2215/202—Containing nitrogen-to-oxygen bonds containing nitro groups
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- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
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- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
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- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/02—Esters of silicic acids
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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- C10N2010/02—Groups 1 or 11
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- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
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- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
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- C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
- C10N2060/04—Oxidation, e.g. ozonisation
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- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Definitions
- The'pre'sent invention relates to anew type ofsynthetic lubiicating composition which comprises the formalis' of a wide range of organic compounds which contain at least one free' hydroxyl group" and which is alcoholic in nature and which contains at least" three CH"2O"-"1inkages. 7 p v It' has been'gene'rally accepted by the art that most acetals are not of'sufiieie'nt stability to serve as lubri'cat ing compositions; lt h'as'now beeri'foiind, however, and
- a and B represent the organic compounds less the hydroxyl group.
- x and n represent numbers having a value of 2 or more and y is 1 or more.
- the radicals may be alike or different and may contain from 1 to 60 carbon atoms.
- a and B are selected such that the total number of carbon atoms in the formal is between about 20 and 130,. with compounds containing fromv about 25 to carbon atoms being preferred.
- the organic hydroxy compounds which serve as a source for the radicals A and B will be definedmore in detail below.
- a lubricating composition For use in reciprocating engines, particularly as a lubricant for automotive engines, a lubricating composition must meet several requirements; In order to form an effective lubricating film and to maintain that film at low and high temperatures it must have certain viscosity characteristics. At low temperatures thelubricant must be sufiiciently labile to flow through: the circulatory system of the equipment and allowmovement of lubricated surfaces without an undue power requirement.
- a lubricant having an ASTM pourpoint below about 35 F. has suflicient low temperature l'ahilit'y to make it satisfactory in these respects. for general. use.
- a lubricant must hay'e sufii'cient body or thickness to furnish and maintain a: satisfactory lubricating film. It has been found that a lubricant that is satisfactory in this respect willl have: a viscosity at 210 F. of between about 2 to 60 centistokes, i. c. 32.8 and 280 Saybolt seconds, Universal; T e prevent undue lubricant loss, due to volatility" and general molecular disintegration and to insure againstiexplosion hazards at higher temperatures sometimesencounteredg a lubricating composition should have a flasli point in eXcess-of about 300 F. These requisites are inherent in the term lubricating compositions, as used in.
- the reactants may b'e adriibced in the reacting zone and heated to reflux temperature in the presence of an entraining agent such" as' hexane", heptane or the like. After recovery of the water of theory the product is washed free of any acidi'c ca'talysts and stripped free of unreacted components.
- Polyethylene glycols (a) Diethylene glycol 51;) Triethylene glycol c) Tetraethylene glycol 2.
- Polypropylene glycols (a) Dipropylene glycol (b) Tripropylene glycol sh) 1,2-cyclohexanedio1 i) Decanedi0l-1.10 2.
- Other polyhydric alcohols (11) Glycerol (b) 2hydroxymethyl-2-methyl-propanedlol-I,3 (c) Pentaerythritol I v d orbitol e) Dipentaerythritol f) Dulcitol Trimethylol propane 'letramethylol cyclohexanol t) Benzotrimethylol II.
- Substituted alcohols Monohydric 1. Aliphatic (a) Halogenated alcohols 1. Ethylene chlorohydrin 2. Trlfluoro ethanol 3. Propylene chlorohydrln 4. The various chloro-substltuted monoethers of polyalkylene glycols Ethanolamine 2-amino propanol 2-m'troethanol 2-nitropropanol 2-nitrobutanol The various glycol monoesters, e. g. 1. Ethylene glycol monoacetate 2. Propylene glycol monobutyrate Butylene glycol monolaurate Polyethylene glycol monoesters Polypropylene glycol monoesters Polybutylene glycol monoesters he various glycol monoethers, e. g.
- a-Hydroxy adipaldehvde 2.
- B-Hydroxy propionaldehyde Particularly desirable organic hydroxy compounds for use in this invention are those highly branched chain aliphatic alcohols prepared by the OX0 synthesis.
- This Oxo synthesis may be described as being the catalytic reaction of an olefin with carbon monoxide and hydrogen. The reaction occurs at temperatures in the order of 300400 F., at pressures in the range of about 1000 to 3000 p. s. i., in the presence of a suitable catalyst, ordinarily a heavy metal carbonyl such as cobalt carbonyl.
- the resulting aldehyde is subsequently hydrogenated to a primary alcohol. This process is described in U. S. Patent No. 2,327,066 issued to Roelen in 1943.
- phosphoric acid catalysts such as phosphoric acid or copper phosphate impregnated on silica gel, sulfuric acid, Friedel- Crafts catalysts, activated clays, silica-alumina, copper pyrophosphate, etc.
- Suitable conditions when employing phosphoric acid catalysts of the U. 0. P. type are temperatures of 300 F. to 500 F., pressures from 250 to 5,000 p. s. i. and feed stocks comprising refinery streams containing propylene and mixed butylenes.
- Suitable feed stocks for example, may contain from to 60 mol percent propylenes, from 0.5 to 15 mol percent butylenes, and from 0.1 to 10 mol percent isobutylene, the remaining being saturated hydrocarbons.
- Other suitable feed stocks are the dimer and trimer of isobutylene.
- the prefenred Ox'o alcohols employed in forming the formals of this invention are those having from 8 to carbon atoms derived from olefin copolymers having from 7 to 19 carbon atoms.
- the desired olefin fraction is segregated from the crude olefin polymer product by fractionation.
- the following table shows the structure and percent composition of Ca OX0 alcohols prepared from a. C7 olefin stream which had been fractionated from the products obtained by the phosphoric acid polymerization of refinery gas streams containing propylene and mixed nand isobutylenes.
- complex form'als may be considered to have the following general formula:
- a and B represent radicals derived from organic compounds by removal of one reacting h'y'droxyl group.
- x and n are 2 or more and y is one or more.
- the radicals represented by A and -B may be alike or different and may contain fromxl to 60' carbon atoms. The sum of the carbon atoms in -the molecule should be between 20 and 130 and .pre'ferablyzbetween about and 100. 1.
- the grou of organic compounds that satisfy th'eeonditions of the above generic formula and that are used to build the preferred compounds according to the concept of this invention are monohydric alcohols, glycols, and organic acids. These compounds may be advantageously combined with formaldehyde to form molecules having the following type formulas, words instead of structures being given to show the components of the complex formals.
- glycol monoester-(formaldehyde-glycol) a Glycol monoeth'e'r-(formaldehyde-glycol)m
- x represents a Whole number greater than 11.
- the acids which may be used to prepare the glycol monoesters may be selected from the following partial list:
- n-ctin ocrncHz 2ocuzocsneocansocgneonn
- the hemiformal of n-butyl Carbitol was made by heating 81.1 g. /z mole) of the Carbitol with 15.1 g. /2 mole CH2O) of paraformaldehyde, 200 g. of heptane and 2 g. of NaHSO4 at 65 C. for half an hour.
- a and B may be the same or diiferent and are selected from the group consisting of organic radicals containing from 1 to 60 carbon atoms which corresponds to organic compounds containing a hydroxyl group that is alcoholic in nature and wherein x and n are whole numbers greater than 1 and y is 1 or more.
- the reaction product was decanted from the catalyst and then washed with 150 cc. of NazCOa solution and finally with two 100 cc. portions of water. The material was then stripped free of the solvent and light ends.
- the material boiling above 152 C. at 0.3 mm. pressure and consisting of the 14100% fraction had the following proper-ties:
- the material obtained boiling above 161 C. at 0.3 mm. had the following properties:
- This product was purified in the manner similar to that of Example VI above and stripped to 210 C. vapor temperature at 9.0 mm. pressure.
- This product had the following properties:
- the complex formals as describedherein may serve as the lubricant base for grease compositions.
- These syntheticlubricants may be thickened to stable grease structures with conventional grease forming soaps such as lithium soaps of high molecular weightsubstantially saturated fatty acid, the n-acyl p am'ino phenols, silica gels, treated bentinites and the like. Oxidation inhibitors, rust inhibitors, tackiness agents and other grease addition agents may be added to the complex formal greases.
- the soap complexes known to the artmade by using low molecular weight acid salts may also be used in preparing these grease compositions.
- the complex formals of this invention may be blended with mineral oil or other synthetic lubricants such as simple bis-formals, complex esters, di-esters, phosphates, siloxanes, silicates, phosphonates and the like and a grease composition which incorporates the desirable characteristics of the blends may be prepared by conventional techniques.
- mineral oil or other synthetic lubricants such as simple bis-formals, complex esters, di-esters, phosphates, siloxanes, silicates, phosphonates and the like and a grease composition which incorporates the desirable characteristics of the blends may be prepared by conventional techniques.
- this invention relates to new compositions of matter which have outstanding utility as synthetic lubricating compositions.
- the materials contemplated may be broadly described as being complex formals of organic materials containing at least one hydroxyl group that is alcoholic in nature.
- complex formal is meant materials containing more than 2 formal linkages.
- the structure of the formals of invention may be described as one corresponding to the formula:
- a and B are organic radicals containing from 1 to 60 carbon atoms which are derived from organic materials containing at least one hydroxyl group that is alcoholic in nature.
- a and B may be alike or different and the total number of carbon atoms in the molecule should be between about 20 and 130, preferably between about 25 and 100.
- the compounds that are especially preferred and that are considered to be the preferred embodiment of this invention are those materials that have a kinematic viscosity at 210 F. within the range of from 2 to 60 centistokes, an ASTM pour point of at least as low as 35 F., and a flash point of at least 300 F.
- solubilizers grease bases, insecticides, weed killers, rust preventives, solvents, .dewaxing aids, detergents, and as raw materials for many other industrial applications, such as household -detergents, fumigants, etc.
- These new synthetic lubricating oils may be admixed with other lubricating oils, naturally occurring or synthetic, either as concentratesor as finished blends. They are compatible and may bev blended with the well known lubricant addition agents such as viscosity index improvers, pour point depressors, detergents, rust inhibitors, antioxidants, and the like.
- a complex formal having an ASTM pour point below about 35 F., a flash point above about 300 F., and a kinematic viscosity at 210 F. within the range of from 2 to 60 centistokes, said formal corresponding to the formula wherein A and B are selected from the group consisting of hydrocarbon and substituted hydrocarbon radicals containing from 1 to 60 carbon atoms wherein at and n are integers having a value of at least 2 and y is an integer having a value of at least 1, the total number of carbon atoms in the molecule being between and 130.
- a synthetic lubricant according to claim 1 wherein A is derived from monohydric alcohol and wherein B is derived from a glycol.
- a complex formal having the formula wherein A and B are organic radicals derived from C8 to C20 alcohols and wherein x and n are numbers having the value of 2 or more and y is an integer having a value of at least 1, said formal being formed by reacting together x.y moles of a glycol with x-I-l moles of formaldehyde and 2 moles of an alcohol containing from 8 to 20 carbon atoms, said formal having an ASTM pour point below about +35 F., a flash point above about 300 F., and a viscosity at 210 F. within the range of from 2 to 60 centistokes, the total number of carbon atoms in the molecule being between about to 100.
- a synthetic lubricant according to claim 4 wherein said glycol is tripropylene glycol.
- a synthetic lubricant according to claim 4 wherein said alcohol is a highly branchedchain aliphatic alcohol of 13 carbon atoms alcohol and wherein x, n, and y are 3.
- a synthetic lubricant according to claim 4 wherein said alcohol is an ether alcohol, wherein said glycol is a polypropylene glycol of a molecular weight of about 150 and wherein x is 2.
- a synthetic lubricant according to claim 4 having an ASTM pour point of below l5 F., a flash point in excess of 350 F. and viscosity at 210 F. of from 2.6 to 13.0 centistokes.
- a complex formal of the formula wherein A and B are selected from the group consisting of hydrocarbon and substituted hydrocarbon radicals containing from 1 to carbon atoms and wherein x and n are numbers having the value of at least 2 and wherein y is a number of at least 1 thickened to a grease consistency with a lithium soap of a high molecular weight fatty acid, said complex formal having an ASTM pour point below about +35 F., a flash point above about 300 F., and a viscosity at 210 F. within the range of from 260 centistokes, the total number of carbon atoms in said formal being between about 20 to 130.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
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- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NLAANVRAGE7807232,A NL181914B (nl) | 1952-11-29 | Inrichting voor het vervaardigen van getrokken voorwerpen. | |
| NL89229D NL89229C (enrdf_load_html_response) | 1952-11-29 | ||
| US323338A US2796401A (en) | 1952-11-29 | 1952-11-29 | Complex formal lubricating composition |
| DEST7387A DE961483C (de) | 1952-11-29 | 1953-11-28 | Synthetisches Schmiermittel |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US323338A US2796401A (en) | 1952-11-29 | 1952-11-29 | Complex formal lubricating composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2796401A true US2796401A (en) | 1957-06-18 |
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ID=23258784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US323338A Expired - Lifetime US2796401A (en) | 1952-11-29 | 1952-11-29 | Complex formal lubricating composition |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2796401A (enrdf_load_html_response) |
| DE (1) | DE961483C (enrdf_load_html_response) |
| NL (2) | NL181914B (enrdf_load_html_response) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3005774A (en) * | 1957-07-29 | 1961-10-24 | Exxon Research Engineering Co | Lubricants containing cross-linked polymers as thickening agents |
| US3205269A (en) * | 1960-05-10 | 1965-09-07 | Union Carbide Corp | Stabilization of ethers with phosphorous compounds |
| US3231604A (en) * | 1962-01-23 | 1966-01-25 | Du Pont | Polyethylene oxide and polypropylene oxide perfluoroalkyl substituted oxyalkanoates |
| US3249543A (en) * | 1963-04-30 | 1966-05-03 | Monsanto Res Corp | Lubricant composition containing a rhodanine compound |
| US3392118A (en) * | 1966-06-09 | 1968-07-09 | Sinclair Research Inc | Formal of diene polymer containing terminal hydroxyl groups and mineral oil containing same |
| US3435077A (en) * | 1965-01-16 | 1969-03-25 | Huels Chemische Werke Ag | Process for the production of asymmetrical formals |
| US3875197A (en) * | 1968-07-15 | 1975-04-01 | Hoechst Ag | Amido-methyl-polyglycol formals |
| US3900411A (en) * | 1973-11-19 | 1975-08-19 | Mobil Oil Corp | Lubricant compositions containing acetal or ketal detergents |
| US4093666A (en) * | 1974-02-06 | 1978-06-06 | Hoechst Aktiengesellschaft | Process for the manufacture of glycol ether formals |
| US4189609A (en) * | 1974-08-19 | 1980-02-19 | Basf Wyandotte Corporation | Multi-block coupled polyoxyalkylene copolymer surfactants |
| US4408084A (en) * | 1981-01-09 | 1983-10-04 | Basf Wyandotte Corporation | Non-ionic surfactants containing acetal groups |
| US5744065A (en) * | 1995-05-12 | 1998-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Aldehyde-based surfactant and method for treating industrial, commercial, and institutional waste-water |
| US5744064A (en) * | 1995-05-12 | 1998-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Ketone-based surfactant and method for treating industrial, commerical, and institutional waste-water |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1059599B (de) * | 1953-05-28 | 1959-06-18 | Exxon Research Engineering Co | Synthetische Schmiermittel |
| DE1121759B (de) * | 1954-03-17 | 1962-01-11 | Exxon Research Engineering Co | Synthetisches Schmiermittel |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2350350A (en) * | 1941-05-06 | 1944-06-06 | Du Pont | Glycol formals |
| US2379703A (en) * | 1942-04-24 | 1945-07-03 | Richards Chemical Works Inc | Process for the production of derivatives of polyhydroxy alcohols |
| US2397602A (en) * | 1941-11-22 | 1946-04-02 | Du Pont | Preparation of ester polymers |
| US2436347A (en) * | 1944-12-30 | 1948-02-17 | Standard Oil Dev Co | Grease compositions |
| US2473994A (en) * | 1945-08-04 | 1949-06-21 | Du Pont | 1, 3-dioxolane polymers |
| US2594341A (en) * | 1949-09-13 | 1952-04-29 | Standard Oil Dev Co | Utilization of oxo bottoms |
-
0
- NL NL89229D patent/NL89229C/xx active
- NL NLAANVRAGE7807232,A patent/NL181914B/xx unknown
-
1952
- 1952-11-29 US US323338A patent/US2796401A/en not_active Expired - Lifetime
-
1953
- 1953-11-28 DE DEST7387A patent/DE961483C/de not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2350350A (en) * | 1941-05-06 | 1944-06-06 | Du Pont | Glycol formals |
| US2397602A (en) * | 1941-11-22 | 1946-04-02 | Du Pont | Preparation of ester polymers |
| US2379703A (en) * | 1942-04-24 | 1945-07-03 | Richards Chemical Works Inc | Process for the production of derivatives of polyhydroxy alcohols |
| US2436347A (en) * | 1944-12-30 | 1948-02-17 | Standard Oil Dev Co | Grease compositions |
| US2473994A (en) * | 1945-08-04 | 1949-06-21 | Du Pont | 1, 3-dioxolane polymers |
| US2594341A (en) * | 1949-09-13 | 1952-04-29 | Standard Oil Dev Co | Utilization of oxo bottoms |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3005774A (en) * | 1957-07-29 | 1961-10-24 | Exxon Research Engineering Co | Lubricants containing cross-linked polymers as thickening agents |
| US3205269A (en) * | 1960-05-10 | 1965-09-07 | Union Carbide Corp | Stabilization of ethers with phosphorous compounds |
| US3231604A (en) * | 1962-01-23 | 1966-01-25 | Du Pont | Polyethylene oxide and polypropylene oxide perfluoroalkyl substituted oxyalkanoates |
| US3249543A (en) * | 1963-04-30 | 1966-05-03 | Monsanto Res Corp | Lubricant composition containing a rhodanine compound |
| US3435077A (en) * | 1965-01-16 | 1969-03-25 | Huels Chemische Werke Ag | Process for the production of asymmetrical formals |
| US3392118A (en) * | 1966-06-09 | 1968-07-09 | Sinclair Research Inc | Formal of diene polymer containing terminal hydroxyl groups and mineral oil containing same |
| US3875197A (en) * | 1968-07-15 | 1975-04-01 | Hoechst Ag | Amido-methyl-polyglycol formals |
| US3900411A (en) * | 1973-11-19 | 1975-08-19 | Mobil Oil Corp | Lubricant compositions containing acetal or ketal detergents |
| US4093666A (en) * | 1974-02-06 | 1978-06-06 | Hoechst Aktiengesellschaft | Process for the manufacture of glycol ether formals |
| US4189609A (en) * | 1974-08-19 | 1980-02-19 | Basf Wyandotte Corporation | Multi-block coupled polyoxyalkylene copolymer surfactants |
| US4408084A (en) * | 1981-01-09 | 1983-10-04 | Basf Wyandotte Corporation | Non-ionic surfactants containing acetal groups |
| US5744065A (en) * | 1995-05-12 | 1998-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Aldehyde-based surfactant and method for treating industrial, commercial, and institutional waste-water |
| US5744064A (en) * | 1995-05-12 | 1998-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Ketone-based surfactant and method for treating industrial, commerical, and institutional waste-water |
| US5851434A (en) * | 1995-05-12 | 1998-12-22 | Union Carbide Chemicals & Plastics Technology Corporation | Ketone-based surfactant and method for treating industrial, commercial, and institutional waste-water |
| US5919372A (en) * | 1995-05-12 | 1999-07-06 | Union Carbide Chemicals & Plastics Technology Corporation | Aldehyde-based surfactant and method for treating industrial commercial and institutional waste-water |
| US6051035A (en) * | 1995-05-12 | 2000-04-18 | Union Carbide Chemicals & Plastics Technology Corporation | Methods of cleaning fabrics with splittable aldehyde-based surfactants |
| US6306249B1 (en) | 1995-05-12 | 2001-10-23 | Union Carbide Chemicals & Plastics Technology Corporation | Method for treating contaminated surface with aldehyde-based surfactant |
Also Published As
| Publication number | Publication date |
|---|---|
| NL89229C (enrdf_load_html_response) | |
| NL181914B (nl) | |
| DE961483C (de) | 1957-04-04 |
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