US2987527A - Treating compound and method - Google Patents
Treating compound and method Download PDFInfo
- Publication number
- US2987527A US2987527A US793268A US79326859A US2987527A US 2987527 A US2987527 A US 2987527A US 793268 A US793268 A US 793268A US 79326859 A US79326859 A US 79326859A US 2987527 A US2987527 A US 2987527A
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- United States
- Prior art keywords
- lecithin
- diamine
- gasoline
- parts
- composition
- 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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- 238000000034 method Methods 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 title description 16
- 239000000787 lecithin Substances 0.000 claims description 54
- 229940067606 lecithin Drugs 0.000 claims description 54
- 235000010445 lecithin Nutrition 0.000 claims description 53
- 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 claims description 52
- 239000000203 mixture Substances 0.000 claims description 31
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 27
- 229930195729 fatty acid Natural products 0.000 description 27
- 239000000194 fatty acid Substances 0.000 description 27
- -1 diamine compound Chemical class 0.000 description 19
- 150000001412 amines Chemical class 0.000 description 16
- 239000000446 fuel Substances 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 11
- 150000004985 diamines Chemical class 0.000 description 11
- 150000004665 fatty acids Chemical class 0.000 description 11
- 230000008569 process Effects 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 230000009471 action Effects 0.000 description 6
- 239000003254 gasoline additive Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical class CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 4
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- HUTDDBSSHVOYJR-UHFFFAOYSA-H bis[(2-oxo-1,3,2$l^{5},4$l^{2}-dioxaphosphaplumbetan-2-yl)oxy]lead Chemical group [Pb+2].[Pb+2].[Pb+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O HUTDDBSSHVOYJR-UHFFFAOYSA-H 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 229940083466 soybean lecithin Drugs 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- YUWBVKYVJWNVLE-UHFFFAOYSA-N [N].[P] Chemical compound [N].[P] YUWBVKYVJWNVLE-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000003026 anti-oxygenic effect Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CURJNMSGPBXOGK-UHFFFAOYSA-N n',n'-di(propan-2-yl)ethane-1,2-diamine Chemical compound CC(C)N(C(C)C)CCN CURJNMSGPBXOGK-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- KFDIDIIKNMZLRZ-UHFFFAOYSA-N n'-propan-2-ylpropane-1,3-diamine Chemical compound CC(C)NCCCN KFDIDIIKNMZLRZ-UHFFFAOYSA-N 0.000 description 1
- 239000002120 nanofilm Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/106—Adducts, complexes, salts of phosphatides
Definitions
- This invention relates to a treating compound and method.
- the compound or composition is particularly useful in the treating of gasoline for the control and reduction of intake system deposits, carburetor cleaning,
- composition is also useful as a releasing, softening and wetting agent in textile manufacture and as a dispersing agent for pigment concentrates in paints and other vehicles.
- the invention is particularly useful as a gasoline additive.
- gasoline additive products with detergency action are available on the market, their use for keeping intake or induction systems and carburetor clean is limited in many respects.
- Most of the synthetic detergents are very expensive or are not compatible with gasoline and with the additives of gasoline, or their detergency action is so strong that the settling out of metallic ions after the treatment of the gasoline by the producer is prevented or delayed, and an emulsion is formed between the gasoline and the water bottoms in storage tanks, with a subsequent loss of valuable additives to the water.
- the individual needs of each gasoline producer are so varied that no single ingredient or compound is suitable 'for adaptation to different optimal conditions.
- An object of this invention is to provide a new composition or treating compound having unique surfacemodifying characteristics as compared with the starting materials.
- a further object of this invention is to provide an economical, effective compound for eliminating the build-up of carburetor and intake manifold deposits during normal vehicle operation when used with gasolines of widely varying composition.
- a still further object is to provide a composition for treating gasoline which is not only compatible with gasolines of widely varying composition but also with gasolines having the common gasoline additives and with substantially no adverse efiect on O.R.I. (octane rating increase) or disturbance to the composition and to the physical characteristics of the gasoline for the beneficial actions of eliminating carburetor and intake manifold deposits, anti-icing, rust control, and other benefits which will be hereinafter set forth.
- Yet another object is to provide a method for the treatment of gasolines of widely varying composition and having therein the common gasoline additives now employed for an effective detergency and prevention of the build-up of carburetor and intake manifold deposits without contributing to the problems that are encountered in the storage of gasoline.
- commercial filtered lecithin containing a low level of benzene-insoluble materials is diluted with petroleum oil such as, for example, 60 neutral oil, a staturated aliphatic hydrocarbon having 'an approximate molecular weight of 150.
- the extending agent, 60 neutral oil improves the viscosity of lecithin and facilitates a uniform contact among the reacting materials.
- an organic base which reacts with the acidic groups of the phosphatides and also neutralizes the residual free fatty acids always present in commercial lecithin preparations.
- the reaction mixture is characterized by 12l5% loss of titratable amines as soon as the lecithin comes into contact with the diamine compound.
- the reactive mixture is allowed to stand for 16 hours at 150 F., there is an approximate loss of 35% titratable amines.
- an equilibrium occurs in storage, with the result that the final product has approximately 40% less titrattable amines than the amount originally present in the reacting ingredients.
- Infrared anaylsis showed a loss in primary and secondary amines after the reaction, with a consequent increase in amide linkages.
- This reaction probably represents several types of amide formation such as ammonolysis of glyceride linkages, dehydration of amine salts of fatty acids, and interaction between the phosphatidic groups of lecithin and the diamine. There is no loss of total nitrogen contact of the reactive mixture during the reaction phase.
- the viscosity of lecithin is reduced from 50,000 centipoises to 2500 centipoises at F. This reduction is more than that which would be caused by a mere dilution effect.
- reaction mixture which reaches substantial equilibrium and which is characterized by a compound containing an amide linkage as determined by infrared spectroscopy and by the simultaneous loss of titratable amines.
- peaks representing the molecular vibration of the diamine compound are completely absent in the reaction mixture, while at the same time the characteristic amide peaks which were absent in the diamine and lecithin now appear.
- the lecithin (to be reacted) is preferably a filtered lecithin, because the unfiltered lecithin product has a high benzene-insoluble residue from impurities (meal, dust, carbohydrates, etc.). Such impurities would lend a hazy appearance to lecithin in solvents, and they would also increase the deposit formation in the engine.
- the lecithin product is obtained by centrifugal separation from crude soybean oil, etc., dried to a moisture value of less than .8%, and filtered to a low benzene-insoluble value.
- the dilution oil may be any petroleum oil that substantially lowers the viscosity of the lecithin and reduces the acetone-insoluble value of the lecithin material to approximately 50-65%.
- the N-aliphatic or alicyclic substituted polymethylenediamines which will be referred to hereinafter as fatty acid diamines, are strong organic bases having strong cationic activity.
- the alkyl group is derived usually from a fatty acid" or from a group of fatty acids such as those obtained by the hydrolysis of coconut oil, soybean oil, tallow, and other animal and vegetable oils.
- the ,diamines preferably contain both primary and secondary aminegroupings.
- Other aliphaticor' aromatic amines and quaternary compounds may also be used, if they are compatible with the gasoline mixture or if their usage is justified by some specified demand that they might fulfill more advantageously than the above-mentioned .
- fatty acid diamines We prefer, however, the fatty acid diamines, because of their effective cationic activity which is operative without disturbing the composition of the gas'olines and the function of their solvents while also avoiding the formation of emulsions, etc.
- the N-alkylated diamines can be any of the materials of the formula in which R can be hydrogen and R and R can be methyl groups as in the case of 3-dimethyl amino pro beneficial results, however, are obtained when the fatty acid diamine is used in the range of 1% to 50%.
- the fatty acid diamine may be combined by weight with the lecithin in the proportion of of diamine to 80% of lecithin.
- Each amino group can contain an alkyl substituent such as in N,N- dimethylethylene-diamine or N,N-diisopropylethylenediamine, or N,N'dimethyl-l,3-propylenediamine, or N,N- diisopropyl-l,3-propylenediamine, or similar compounds.
- the de-icing or anti-icing control is believed to be due to the hydrophobic mono-molecular film which tends to insulate the metal parts from the very sensitive and very volatile gasoline components.
- lecithin in addition to being an anti-oxidant in its own right, has the ability to act synergistically with other materials which show anti-oxygenic activity. For example, it has been shown that lecithin can reenforce tremendously the action of phenolic anti-oxidants. This anti-oxidant property of lecithin is not lost in the lecithin-diamine reaction mixture and can be listed as an important marginal benefit of the invention. This is of particular interest because many of the accepted inhibitors or anti-oxidants that are being offered to the petroleum field today are phenolictype materials. It will also aid in maintaining the lubricating oil in clean condition despite the build-up of combustion products as normally occurs. Finally, because of lower viscosity of the lecithin-diamine reaction mixture, the handling characteristics, storage, transfer, and feeding thereof, are much better than that of ordinary lecithin. 7
- the fatty acid diamine which is to be reacted with the lecithin may be varied in percentage within a substantial range. We prefere to combine by. weight from 10% to 40% of diamine with the lecithin for best results.
- the fatty acid diamine and lecithin are combined by weight in the range of -1% diamine and 10-99% lecithin.
- best results have been obtained when the materials are combined in the proportions of 20-50% of the fatty acid diamine and 80-50% of lecithin.
- the proportions of the lecithin-fatty acid-diamine reactive mixture blended with the gasoline may be in the range of 25-500 parts per million, the preferred range being 50-100 parts per million.
- the fatty acid diamine may be reacted with the lecithin at a temperature and for a period of time to reach substantial equilibrium. Equilibrium is usually reached when there has been a loss of about 30-40% of the titratable amines. We prefer to employ temperatures of about -150 F. for a period of at least 15 minutes, but, if desired, temperatures as low as 32 F. and up to 400 F. may be employed. In the foregoing, a reaction mixture is obtained which is characterized by the formation of amides which constitute at least 10% of the amines derived from the N-aliphatic or alicyclic substituted polymethylene-diamine.
- the resultin reacted mixture gives an optimal surface action so that it is an effective releasing agent in textile manufacture while having an increased softening and wetting effect and, when employed in gasoline, has a marked cleansing effect on the carburetor and the intake system of gasoline engines. It has also excellent anti-icing properties.
- Example I A commercial motor gasoline additive was prepared by blending in a filtered soybean lecithin and coconut fatty acid diamines at the levels of 55 parts per million.
- Example II The process was carried on as described in Example 1 except that only lbs. of coconut fatty acid diamine and 90 lbs. of lecithin (diluted with 60 neutral oil) were .used per 100 lbs. total. The product gave excellent detergency with substantially no tendency for emulsion formation.
- Example 111 The process was carried on as described in Example 1, except that to the lecithin were added'20 lbs. of soya 'fatty acid diamines having a combining molecular weight of 356 and a primary amine content of 40%.
- the product gave excellent anti-icing results while inhibiting corrosion, and the compound is recommended where changing surfaces of metal .from hydrophilic to hydrophobic properties is desired.
- Example IV The process was carried on as described in Example III except that 20 lbs. of the monoand dioleate salts of tallow fatty acid diamines were added to the diluted lecithin. The product was 'found to have strong detergent properties, basteriostatic properties, and corrosioninhibiting properties.v
- Example V The effect of the lecithin-diamine reaction mixture in maintaining carburetors-in a-clean condition and in cleaning carburetors which have become dirty, can be seen from this and the following example:
- the cleanliness of the carburetors was rated by visual inspcction on an arbitrary scale comparable to the L4 varnish range scale, a rating 10 being assigned to a clean carburetor and a rating 0 being assigned to an extremely dirty carburetor fouled to the point of practical From this it will be seen that in trucks starting the test with clean carburetors, they became markedly dirtier when the base fuel did not contain the additive. In the trucks which started the test with dirty carburetors, the carburetors became dirtier on the fuel without the additive, but became appreciably cleaner when operated on the fuel with the additive.
- Example VI In this example, three cars were employed to determine the effect of the additive in both city stop-and-go type driving and in sustained high speed driving, "such as encountered on turnpikes. Each car went through three phases, as follows:
- Phase I was designed to build up deposits in a car starting with a clean carburetor.
- the car was driven 400 miles on the same base fuel as in Example V, utilizing the following cycle: One mile at 25 miles per-hour, 5 minutes with a car idling ina .closed garage (breathing its own exhaust), 10 minutes with the engine turned oif, sitting in the garage in the presence of the exhaust fumes (which permitted the deposits to solidify). This cycle was repeated 400 times on a round-the-clock basis.
- phase H the car with the deposits built up as above described was driven 400 miles, typical of stopand-go city driving, stabilizing the deposits.
- the car was driven through dense city traffic, with many stop lights, never exceeding 35 miles per hour.
- phase III the car was driven 4,000 miles on a turnpike at 65 miles per hour, with full acceleration after a stop at each service plaza.
- the carburetors were rated at the beginning, at the end of phase I, at the end of phase II, and after each 1,000 miles in phase III, utilizing the same rating scale as in Example V.
- the Ford car was driven throughout on the base fuel; the Pontiac car was driven on the base fuel in phase I, and on base fuel plus 0.005% of the additive of the previous example in phases II and III; and the Madison car was driven on the base fuel in phase I and on the base fuel plus 0.01% of the additive in phases II and III.
- the results are as follows:
- a surface-modifying composition comprising a reaction mixture resulting from the reaction of 10-99 parts by weight of lecithin with 90-1 parts of N-alkyl substituted polymethylene-diamine, with the structural formula of RI I-(CH2)x--NHz in which the alkyl groups are derived from fatty acids, reacted at a temperature and for a time to reach substantial equilibrium, characterized by the formation of amides which constitute at least 10% of the amines derived from said polymethylene-diamine, and by the corresponding decrease in titratable amines.
- composition of claim 1 in which the lecithin is 50-80 parts of the polymethylene-diamine is 50-20 parts.
- composition of claim 1 in which the lecithin is about 80 parts and the polymethylene-diamine is about 20 parts.
- composition of claim 1 in which the lecithin is 1-50 parts and the polymethylene-diamine is 99-50 parts.
- composition of claim 1 in which the lecithin is diluted with an aliphatic hydrocarbon to an acetoneinsoluble value of about 50-65%.
- a surface-modifying composition adapted to be added to gasoline comprising the reaction mixture of 10-80 parts by weight of lecithin with 90-20 parts of an N-alkyl substituted propylene diamine in which the alkyl groups are derived from fatty acids having a chain length of C to C reacted at a temperature and for a time to reach an equilibrium, characterized by the formation of amides which constitute at least 10% of the amines derived from said propylene diamine and by the corresponding decrease in titratable amines.
- a surface-modifying composition comprising a reacted mixture of soy lecithin with an N-alkylsubstituted polymethylene-diamine.
- a treating compound for gasoline comprising a reaction mixture resulting from the reaction of 50-99 parts by weight of lecithin with 1-50 parts of an N-alkyl substituted polymethylene-diamine having the formula of in which the alkyl groups are derived from fatty acids, characterized by the formation of amides which constitute at least 10% of the amines derived from said polymethylene-diamine, as determined by infrared spectroscopy.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
Description
United States Patent 2,987,527 TREATING COMPOUND AND METHOD Donald E. Sincroft, Fort Wayne, and Endre F. Sipos, Decatur, Ind., assignors to Central Soya Company, Inc., Fort Wayne, Ind a corporation of Indiana No Drawing. Filed Feb. 16, 1959, Ser. No. 793,268 17 Claims. (Cl. 260-403) This invention relates to a treating compound and method. The compound or composition is particularly useful in the treating of gasoline for the control and reduction of intake system deposits, carburetor cleaning,
rust and Corrosion control, anti-icing, bacteriostatic action, and other results. The composition is also useful as a releasing, softening and wetting agent in textile manufacture and as a dispersing agent for pigment concentrates in paints and other vehicles.
This application is a continuation-in-part of our copending application, Serial No. 695,540, filed November 12, 1957.
The invention is particularly useful as a gasoline additive. Although numerous gasoline additive products with detergency action are available on the market, their use for keeping intake or induction systems and carburetor clean is limited in many respects. Most of the synthetic detergents are very expensive or are not compatible with gasoline and with the additives of gasoline, or their detergency action is so strong that the settling out of metallic ions after the treatment of the gasoline by the producer is prevented or delayed, and an emulsion is formed between the gasoline and the water bottoms in storage tanks, with a subsequent loss of valuable additives to the water. Furthermore, the individual needs of each gasoline producer are so varied that no single ingredient or compound is suitable 'for adaptation to different optimal conditions.
An object of this invention is to provide a new composition or treating compound having unique surfacemodifying characteristics as compared with the starting materials. A further object of this invention is to provide an economical, effective compound for eliminating the build-up of carburetor and intake manifold deposits during normal vehicle operation when used with gasolines of widely varying composition. A still further object is to provide a composition for treating gasoline which is not only compatible with gasolines of widely varying composition but also with gasolines having the common gasoline additives and with substantially no adverse efiect on O.R.I. (octane rating increase) or disturbance to the composition and to the physical characteristics of the gasoline for the beneficial actions of eliminating carburetor and intake manifold deposits, anti-icing, rust control, and other benefits which will be hereinafter set forth. Yet another object is to provide a method for the treatment of gasolines of widely varying composition and having therein the common gasoline additives now employed for an effective detergency and prevention of the build-up of carburetor and intake manifold deposits without contributing to the problems that are encountered in the storage of gasoline. Other specific objects and advantages will appear as the specification proceeds.
In one embodiment of the invention, commercial filtered lecithin containing a low level of benzene-insoluble materials is diluted with petroleum oil such as, for example, 60 neutral oil, a staturated aliphatic hydrocarbon having 'an approximate molecular weight of 150. The extending agent, 60 neutral oil, improves the viscosity of lecithin and facilitates a uniform contact among the reacting materials. To the diluted lecithin body is then added an organic base which reacts with the acidic groups of the phosphatides and also neutralizes the residual free fatty acids always present in commercial lecithin preparations.
Patented June 6, 1961 In the practice of our invention, lecithin is brought into contact with N-aliphatic or alicyclic substituted polymethylene-diamines with the structural formula of in which the alkyl groups are derived from fatty acids. We prefer to employ an N-alkyl substituted propylene diamine. As a result of the foregoing, there is formed a reaction mixture which may be effectively employed with gasolines of widely varying composition and containing the common gasoline additives so as to bring about an effective detergency action without contributing to emulsion problems in the storage tanks and providing bacteriostatic action in the water bottoms. Moreover, the reaction mixture is found to have an anti-icing effect. The reaction mixture is characterized by 12l5% loss of titratable amines as soon as the lecithin comes into contact with the diamine compound. When the reactive mixture is allowed to stand for 16 hours at 150 F., there is an approximate loss of 35% titratable amines. After this sudden decrease of 35% titratable amines in the reaction mixture, an equilibrium occurs in storage, with the result that the final product has approximately 40% less titrattable amines than the amount originally present in the reacting ingredients. Infrared anaylsis showed a loss in primary and secondary amines after the reaction, with a consequent increase in amide linkages. This reaction probably represents several types of amide formation such as ammonolysis of glyceride linkages, dehydration of amine salts of fatty acids, and interaction between the phosphatidic groups of lecithin and the diamine. There is no loss of total nitrogen contact of the reactive mixture during the reaction phase.
The viscosity of lecithin is reduced from 50,000 centipoises to 2500 centipoises at F. This reduction is more than that which would be caused by a mere dilution effect.
There are, probably numerous other physico-chemical changes in addition to the foregoing, when one considers the complex nature of commercial soybean lecithin, but it is believed not necessary from the point of view of performance to go into such detailed characterization.
In the combining of the lecithin and diamine, as above described, there is formed a reaction mixture which reaches substantial equilibrium and which is characterized by a compound containing an amide linkage as determined by infrared spectroscopy and by the simultaneous loss of titratable amines. At 8.85 microns, the peaks representing the molecular vibration of the diamine compound are completely absent in the reaction mixture, while at the same time the characteristic amide peaks which were absent in the diamine and lecithin now appear.
The lecithin (to be reacted) is preferably a filtered lecithin, because the unfiltered lecithin product has a high benzene-insoluble residue from impurities (meal, dust, carbohydrates, etc.). Such impurities would lend a hazy appearance to lecithin in solvents, and they would also increase the deposit formation in the engine. The lecithin product is obtained by centrifugal separation from crude soybean oil, etc., dried to a moisture value of less than .8%, and filtered to a low benzene-insoluble value.
The dilution oil may be any petroleum oil that substantially lowers the viscosity of the lecithin and reduces the acetone-insoluble value of the lecithin material to approximately 50-65%.
The N-aliphatic or alicyclic substituted polymethylenediamines, which will be referred to hereinafter as fatty acid diamines, are strong organic bases having strong cationic activity. The alkyl group is derived usually from a fatty acid" or from a group of fatty acids such as those obtained by the hydrolysis of coconut oil, soybean oil, tallow, and other animal and vegetable oils. The ,diamines preferably contain both primary and secondary aminegroupings. Other aliphaticor' aromatic amines and quaternary compounds may also be used, if they are compatible with the gasoline mixture or if their usage is justified by some specified demand that they might fulfill more advantageously than the above-mentioned .fatty acid diamines. We prefer, however, the fatty acid diamines, because of their effective cationic activity which is operative without disturbing the composition of the gas'olines and the function of their solvents while also avoiding the formation of emulsions, etc.
The N-alkylated diamines can be any of the materials of the formula in which R can be hydrogen and R and R can be methyl groups as in the case of 3-dimethyl amino pro beneficial results, however, are obtained when the fatty acid diamine is used in the range of 1% to 50%. As a: specific example, the fatty acid diamine may be combined by weight with the lecithin in the proportion of of diamine to 80% of lecithin.
While, from the standpoint of Id'etergencyand other uses described herein, we have found the proportions of l-50% of the fatty acid diamine with 99-50% ofthe lecithin eflicacious, our preferredrange is 20-50% ofrthe fatty acid diamine compound and 80-50% of lecithin.- And where the reaction mixture is employed specifically for de-icing and other special uses, the proportions may be further varied in the range of 90-20% of the fatty pylamine. Similarly, R can be hydrogen and R and R can be ethyl groups or other alkyl groups containing l-4carbon atoms, as in the case of 3-diethyl amino propylamine or 3-isopropylaminopropylamine. Each amino group can contain an alkyl substituent such as in N,N- dimethylethylene-diamine or N,N-diisopropylethylenediamine, or N,N'dimethyl-l,3-propylenediamine, or N,N- diisopropyl-l,3-propylenediamine, or similar compounds.
While the specific operation of the organic base-lecithin reacted mixture for carrying out the above results is not completely understood, it is believed that the complex is preferentially adsorbed from the solvent onto metal surfaces even in the presence of Water, and that the complex plates out on a metal surface as closely packed monomolecular films and forms a highly effective diffusion barrier. This barrier film apparently serves as a chemical insulator by preventing further deposition of particles having afiinity to metal surfaces, thereby acting as an anti-icer, carburetor and intake manifold cleanser, and inhibiting corrosion, spark plug fouling conditions, and controlling surface ignition. The presence of phosphorus works synergistically with other phosphorus addi tives in converting the lead deposits to the lead orthophosphate form. In the lead orthophosphate form, the deposits have a higher glow point, and, therefore, provide a less critical condition that would promote the surface ignition firings.
The de-icing or anti-icing control is believed to be due to the hydrophobic mono-molecular film which tends to insulate the metal parts from the very sensitive and very volatile gasoline components. 7
It should also be pointed out that lecithin, in addition to being an anti-oxidant in its own right, has the ability to act synergistically with other materials which show anti-oxygenic activity. For example, it has been shown that lecithin can reenforce tremendously the action of phenolic anti-oxidants. This anti-oxidant property of lecithin is not lost in the lecithin-diamine reaction mixture and can be listed as an important marginal benefit of the invention. This is of particular interest because many of the accepted inhibitors or anti-oxidants that are being offered to the petroleum field today are phenolictype materials. It will also aid in maintaining the lubricating oil in clean condition despite the build-up of combustion products as normally occurs. Finally, because of lower viscosity of the lecithin-diamine reaction mixture, the handling characteristics, storage, transfer, and feeding thereof, are much better than that of ordinary lecithin. 7
The fatty acid diamine which is to be reacted with the lecithin may be varied in percentage within a substantial range. We prefere to combine by. weight from 10% to 40% of diamine with the lecithin for best results. Some acid diamine and 10-80% of lecithin, as set forth in greater detail in the copending application of Richard J. De Gray, filed on even date herewith as serial No. 793,- 252, and entitled Anti-stalling Additives and Motor Fuel Containing the Same.
From the foregoing and for all uses, the fatty acid diamine and lecithin are combined by weight in the range of -1% diamine and 10-99% lecithin. As already stated, best results have been obtained when the materials are combined in the proportions of 20-50% of the fatty acid diamine and 80-50% of lecithin.
The proportions of the lecithin-fatty acid-diamine reactive mixture blended with the gasoline may be in the range of 25-500 parts per million, the preferred range being 50-100 parts per million.
In the operation of the process, by way of example, the fatty acid diamine may be reacted with the lecithin at a temperature and for a period of time to reach substantial equilibrium. Equilibrium is usually reached when there has been a loss of about 30-40% of the titratable amines. We prefer to employ temperatures of about -150 F. for a period of at least 15 minutes, but, if desired, temperatures as low as 32 F. and up to 400 F. may be employed. In the foregoing, a reaction mixture is obtained which is characterized by the formation of amides which constitute at least 10% of the amines derived from the N-aliphatic or alicyclic substituted polymethylene-diamine.
By proportioning the amount of fatty acid diamine and lecithin, it is found that a selected surface-modifying action can be obtained to meet specific critical requirements and which is significantly different from the activity of the reacting ingredients.
The resultin reacted mixture gives an optimal surface action so that it is an effective releasing agent in textile manufacture while having an increased softening and wetting effect and, when employed in gasoline, has a marked cleansing effect on the carburetor and the intake system of gasoline engines. It has also excellent anti-icing properties.
. Specific examples of the compound and mode of treatment may be set out as follows:
Example I A commercial motor gasoline additive was prepared by blending in a filtered soybean lecithin and coconut fatty acid diamines at the levels of 55 parts per million.
had the following general formula:
H H H R-N-G-tii-t'i-N-H a a it 1'1 a where "R" represents alkyl groups derived from fatty Diarnine- Lecithin Product Lecithin Toluene Moisture-. Free Fatty Acids" Viscosity at 80 F Acetone Insolubl Phosphorus Nitrogen -.do
centipoisem- .percent..
'1 lecithin base diluted with 60-neutrsl 011.
After l6hours of contact at 130 F., there was a 35% loss in titratable amines while infrared analysis showed a loss in primary and'secondary amine content, with -a subsequent increase inamide linkages. As will be noted from the foregoing, the chemical structure, the acidity and viscosity of the lecithin was considerably reduced by the adding of the neutral oil and the coconut diamine. The resulting compound has substantially an ideal polarity for the gasolinemixture, i.e., it is an excellent cleanser for the intake system and carburetor while at the same time the ingredients cooperate in entirely eliminating emulsion problems. The combination of the diamine with the lecithin produces an excellent anti-icing property in addition to the detergency function, rust inhibition, the control of surface ignition, plug fouling, bacteriostatic action in water bottoms, etc.
Example II The process was carried on as described in Example 1 except that only lbs. of coconut fatty acid diamine and 90 lbs. of lecithin (diluted with 60 neutral oil) were .used per 100 lbs. total. The product gave excellent detergency with substantially no tendency for emulsion formation.
Example 111 The process was carried on as described in Example 1, except that to the lecithin were added'20 lbs. of soya 'fatty acid diamines having a combining molecular weight of 356 and a primary amine content of 40%. The product gave excellent anti-icing results while inhibiting corrosion, and the compound is recommended where changing surfaces of metal .from hydrophilic to hydrophobic properties is desired.
Example IV The process was carried on as described in Example III except that 20 lbs. of the monoand dioleate salts of tallow fatty acid diamines were added to the diluted lecithin. The product was 'found to have strong detergent properties, basteriostatic properties, and corrosioninhibiting properties.v
Example V The effect of the lecithin-diamine reaction mixture in maintaining carburetors-in a-clean condition and in cleaning carburetors which have become dirty, can be seen from this and the following example:
A total of 40 trucks operating in the city delivering newspapers were tested; 20 were Ford trucks and 20 were Dodge trucks. Each car was driven for approximately 8,000 miles over a period of approximately 4 months. Ten of the Ford trucks and 10 of the Dodge trucks had clean carburetors at the start of the test, and 10 of the Ford trucks and 10 of the Dodge trucks had normally dirty carburetors at the start of the test. Half of each of the above categories of trucks was operated on a regular gasoline base fuel composed of catalytic -'di'stillate,'catalytic reformate, catalytic polymer, and :straight run naphtha having an octane number'of approximately 90. Half of each of the categories of trucks was operated on the same fuel but containing 0.005% of the additive made in accordance with Example I. The cleanliness of the carburetors was rated by visual inspcction on an arbitrary scale comparable to the L4 varnish range scale, a rating 10 being assigned to a clean carburetor and a rating 0 being assigned to an extremely dirty carburetor fouled to the point of practical From this it will be seen that in trucks starting the test with clean carburetors, they became markedly dirtier when the base fuel did not contain the additive. In the trucks which started the test with dirty carburetors, the carburetors became dirtier on the fuel without the additive, but became appreciably cleaner when operated on the fuel with the additive.
Example VI In this example, three cars were employed to determine the effect of the additive in both city stop-and-go type driving and in sustained high speed driving, "such as encountered on turnpikes. Each car went through three phases, as follows:
Phase I was designed to build up deposits in a car starting with a clean carburetor. In this phase, the car was driven 400 miles on the same base fuel as in Example V, utilizing the following cycle: One mile at 25 miles per-hour, 5 minutes with a car idling ina .closed garage (breathing its own exhaust), 10 minutes with the engine turned oif, sitting in the garage in the presence of the exhaust fumes (which permitted the deposits to solidify). This cycle was repeated 400 times on a round-the-clock basis.
In phase H, the car with the deposits built up as above described was driven 400 miles, typical of stopand-go city driving, stabilizing the deposits. In this test, the car was driven through dense city traffic, with many stop lights, never exceeding 35 miles per hour.
In phase III, the car was driven 4,000 miles on a turnpike at 65 miles per hour, with full acceleration after a stop at each service plaza. The carburetors were rated at the beginning, at the end of phase I, at the end of phase II, and after each 1,000 miles in phase III, utilizing the same rating scale as in Example V.
In the following table, the Ford car was driven throughout on the base fuel; the Pontiac car was driven on the base fuel in phase I, and on base fuel plus 0.005% of the additive of the previous example in phases II and III; and the Plymouth car was driven on the base fuel in phase I and on the base fuel plus 0.01% of the additive in phases II and III. The results are as follows:
Ford Pontiac Plymouth In compounding the treating material with gasoline,
we have obtained efliective results by using the compound in the range of 25 to 500 parts per million. Best .results were obtained when the compound'was blended -lines of widely-varying composition --with substantially no disturbance to the physical characteristics of the gasoline.
While, in the foregoing specification, we have set forth specific steps and ingredients and proportions thereof in considerable detail, it will be understood that such details of procedure, proportions, etc., may be varied Widely by those skilled in the art without departing from the spirit of our invention. 7 7
We claim:
1. A surface-modifying composition, comprising a reaction mixture resulting from the reaction of 10-99 parts by weight of lecithin with 90-1 parts of N-alkyl substituted polymethylene-diamine, with the structural formula of RI I-(CH2)x--NHz in which the alkyl groups are derived from fatty acids, reacted at a temperature and for a time to reach substantial equilibrium, characterized by the formation of amides which constitute at least 10% of the amines derived from said polymethylene-diamine, and by the corresponding decrease in titratable amines.
2. The composition of claim 1 in which the lecithin is 50-80 parts of the polymethylene-diamine is 50-20 parts.
3. The composition of claim 1, in which the lecithin is about 80 parts and the polymethylene-diamine is about 20 parts.
4. The composition of claim 1, in which the lecithin is 1-50 parts and the polymethylene-diamine is 99-50 parts.
5. The composition of claim 1, in which the lecithin is diluted with an aliphatic hydrocarbon to an acetoneinsoluble value of about 50-65%.
6. A surface-modifying composition adapted to be added to gasoline, comprising the reaction mixture of 10-80 parts by weight of lecithin with 90-20 parts of an N-alkyl substituted propylene diamine in which the alkyl groups are derived from fatty acids having a chain length of C to C reacted at a temperature and for a time to reach an equilibrium, characterized by the formation of amides which constitute at least 10% of the amines derived from said propylene diamine and by the corresponding decrease in titratable amines.
7. A surface-modifying composition, comprising a reaction mixture resulting from the reaction of 50-99 parts by weight of lecithin with 1-50 parts of an N-alkyl substituted propylene diamine, in which the alkyl groups are derived from fatty acids having a chain length of C to C reacted at a temperature and for a time to reach an equilibrium, characterized by the formation of amides :which constitut t l ast" of e. m n= ;1fi rom; sai propy e e: d am n a d: b t sa i q s i s decrease in titratable amines. 7? *1 f 8. The composition of claim 7, i' which the alkyl groups of the propylenediamine are derived from the fatty acids obtained by the hydrolysis of coconut oil.
9. A surface-modifying composition, comprising a reacted mixture of soy lecithin with an N-alkylsubstituted polymethylene-diamine. e
10. In a method for preparing a surface-modifying composition, the steps of reacting lecithin with an N-alkyl substituted polymethylene-diamine having thestructural formula f v in which the alkyl groups are derived from fatty acids at a temperature and for a time to reach an equilibrium at-which-20-4-0% of the titratable amines are lost. 'l1.-The process of claim 10, inwhich thereacting 1 temperature is from 32 to 400 F. V 12. The process of claim 10, in which the temperatures 7 are maintained at from 100 to F. and for a period of not less than fifteen minutes. '13, The process of claim 10, in which the proportion of the polymethylene-diamine is from 1-50% by weight. w 14. The process of claim 10, in which the proportion of the polymethylene-diamine is from 10-40% byweight.
15. The process of claim 10, in which the proportion of polymethylene-diamine is about 20% by weight. j 16. In a process for. the preparation of a surface-moditying; composition, the steps of reacting about 80 parts by weight of lecithin with 20 parts by weight. of an N- alkyl substituted polymethylene-diamine with the structural formula of H R -iI-(GHzk-NH, in which the alkyl groups are derived from fatty acids, at a temperature between 32 and 400 F. until equilibrium is obtained, as determined by a reduction in the amine content of from 20-40%.
17. A treating compound for gasoline, comprising a reaction mixture resulting from the reaction of 50-99 parts by weight of lecithin with 1-50 parts of an N-alkyl substituted polymethylene-diamine having the formula of in which the alkyl groups are derived from fatty acids, characterized by the formation of amides which constitute at least 10% of the amines derived from said polymethylene-diamine, as determined by infrared spectroscopy.
References Cited in the file of this patent UNITED STATES PATENTS 2,208,105 Rathbun July 16, 1940 2,295,179 Loane Sept. 8,1942 2,352,760 Bell July 4, 1944 2,839,545 Hennessy et al June 17, 1958 2,885,414 Beal May 5, 1959
Claims (2)
1. A SURFACE-MODIFYING COMPOSITION, COMPRISING A REACTION MIXTURE RESULTING FROM THE REACTION OF 10-99 PARTS BY WEIGHT OF LECITHIN WITH 90-1 PARTS OF N-ALKYL SUBSTITUTED POLYMETHYLENE-DIAMINE, WITH THE STRUCTURAL FORMULA OF
10. IN A METHOD FOR PREPARING A SURFACE-MODIFYING COMPOSITION, THE STEPS OF REACTING LECITHIN WITH AN N-ALKYL SUBSTITUTED POLYMETHYLENE-DIAMINE HAVING THE STRUCTURAL FORMULA
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Cited By (6)
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US3248245A (en) * | 1962-05-17 | 1966-04-26 | Commerical Solvents Corp | Diamine-stabilized adhesive compositions |
US3313607A (en) * | 1964-08-12 | 1967-04-11 | Gulf Research Development Co | Gasoline fuel composition |
US3527584A (en) * | 1966-04-25 | 1970-09-08 | Gulf Research Development Co | Motor fuel multipurpose agents |
US3527583A (en) * | 1966-04-25 | 1970-09-08 | Gulf Research Development Co | Motor fuel multipurpose agents |
US3539601A (en) * | 1967-07-12 | 1970-11-10 | Swift & Co | Fatty amido amines |
US3615291A (en) * | 1966-04-25 | 1971-10-26 | Gulf Research Development Co | Ethoxylated or propoxylated 1,2,4- or 1,2,5-trisubstituted imidazolines and lecithin mixtures and reaction products thereof |
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US2208105A (en) * | 1937-08-28 | 1940-07-16 | Texas Co | Stabilization of light hydrocarbon distillates |
US2295179A (en) * | 1940-10-26 | 1942-09-08 | Standard Oil Co | Lubricating composition and modified addition agent therefor |
US2352760A (en) * | 1941-10-15 | 1944-07-04 | Pure Oil Co | Antiknock compound and motor fuel containing same |
US2839545A (en) * | 1953-11-24 | 1958-06-17 | American Lecithin Company Inc | Processes of phosphorylating phosphatides and products thereof |
US2885414A (en) * | 1957-10-16 | 1959-05-05 | Robert E Beal | Preparation of partial glycerides |
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US2208105A (en) * | 1937-08-28 | 1940-07-16 | Texas Co | Stabilization of light hydrocarbon distillates |
US2295179A (en) * | 1940-10-26 | 1942-09-08 | Standard Oil Co | Lubricating composition and modified addition agent therefor |
US2352760A (en) * | 1941-10-15 | 1944-07-04 | Pure Oil Co | Antiknock compound and motor fuel containing same |
US2839545A (en) * | 1953-11-24 | 1958-06-17 | American Lecithin Company Inc | Processes of phosphorylating phosphatides and products thereof |
US2885414A (en) * | 1957-10-16 | 1959-05-05 | Robert E Beal | Preparation of partial glycerides |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3248245A (en) * | 1962-05-17 | 1966-04-26 | Commerical Solvents Corp | Diamine-stabilized adhesive compositions |
US3313607A (en) * | 1964-08-12 | 1967-04-11 | Gulf Research Development Co | Gasoline fuel composition |
US3527584A (en) * | 1966-04-25 | 1970-09-08 | Gulf Research Development Co | Motor fuel multipurpose agents |
US3527583A (en) * | 1966-04-25 | 1970-09-08 | Gulf Research Development Co | Motor fuel multipurpose agents |
US3615291A (en) * | 1966-04-25 | 1971-10-26 | Gulf Research Development Co | Ethoxylated or propoxylated 1,2,4- or 1,2,5-trisubstituted imidazolines and lecithin mixtures and reaction products thereof |
US3539601A (en) * | 1967-07-12 | 1970-11-10 | Swift & Co | Fatty amido amines |
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