Classifications

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  • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
  • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
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  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/02—Hydroxy compounds
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  • C10M2207/10—Carboxylix acids; Neutral salts thereof
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  • C10M2207/10—Carboxylix acids; Neutral salts thereof
  • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
  • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
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  • C10M2207/10—Carboxylix acids; Neutral salts thereof
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  • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
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Definitions

• This invention relates to novel lub icating oil compositions. More specifically, my invention is concerned with lubricating oil compositions comprising a base oil of lubricating viscosity having incorporated therein certam organic compounds of titanium in an amount sufficient to impart increased load carrying capacity to the base oil. These titanium compounds find particular utility when incorporated in synthetic base oil lubricatmg compositions. In one particular aspect, I have found that the effectiveness of the titanium additives is materially enhanced by the provision of a small amount of free dibasic acid in the lubricant composition.
• the demand for synthetic lubricants is ever increasing In view of, among other things, their low pour point, high viscosity index and low volatility for a given viscosity.
• carrying capacity of lubricating oils can be substantially increased by incorporation of a minor amount ,of a titanium organic compound and the desired characteristics of the base oil'are not deleteriously affected to a material extent.
• the titanium-containing organic materials can be used to impart extreme pressure characteristics to such oils provided for any given use, but most significantly my additives exhibit sufiicient extreme pressure properties in synthetic oils, particularly those consisting essentially of carbon, hydrogen and oxygen, to satisfy specifications, including those of the military, now promulgated or being considered and of which I am aware.
• My additive compounds are further advantageous in that they need not thicken the lubricating oil regardless of the viscosity of the additive since only small amounts of my agents need by employed for most if not all uses.
• the titanium-containing additives of my invention are compatible, i.e. soluble, dispersible or miscible, with the lubricating base oils and have the structure of those products obtained by reacting an organic titanium tetraester with a glycol.
• the additives might be derived from other reactant materials.
• the products can be titanium monomers or polymers, and, if desired, may be waterwashed to approach a water-insensitive form. At least certain of the monomer and polymer additives are chelated and have a coordinate valence bond between an oxygen and a titanium atom.
• the mere addition of a titanium tetraester to a glycol initiates an exothermic reaction, although if desired heating can be employed.
• the reaction may proceed only to the monomer stage or continue to a polymer product directly. If a monomer or partially polymerized product is obtained, it may be further polymerized. In any event, I can employ the various products afforded which range from viscous liquids to solids and are compatible in the base oils.
• alkyl titanates such as methyl, ethyl, propyl, butyl, Z-ethylhexyl, dodecyl, cyclohexyl and ethoxyethyl tetraesters
• aryl tetraesters such as phenyl and betan
• hydrocarbon esters can be substituted in the ester group although the unsubstituted esters are preferred. Those esters prepared from mono-functional alcohols are used most advantageously. Ordinarily the separate organic radicals of the titanium tetraester will contain up to about 12 or 18 carbon atoms but may contain more if desired.
• the additive agents in my lubricant compositions are not limited thereto, the preferred agents are the products obtained through the reaction of the titanium tetraester with a glycol of the 1,3-diol type, see US. Patent No. 2,643,262, hereby incorporated by reference.
• these glycols are 2,3-diorgano hydrocarbon substituted materials which have the formula R-CHOH-(fH-CHzOH
• the diorgano radicals, that is the R and R of the glycol formula can be alkyl, aryl or mixed, and if desired be substituted as with halogen, for instance chlorine.
• R and R should be substantially non-reactive under the reaction and operating conditions employed.
• these glycols contain from about to 12 carbon atoms, for instance an octylene glycol; however, if de sired they could contain a greater number.
• specific glycols which can be employed are 2-ethyl-1,3- hexane-diol, 2-propyl-1,3-heptanediol, 2-methyl-1,3-pentanediol, 2 butyl 1,3 butanediol, 2,4 diphenyl 1,3- butanediol, and 2,4-dimesityl-l,3-butanediol.
• glycols I can employ others and generally the glycols will contain from 2 to about or 24 carbon atoms or more. Also, as indicated above, the glycols may be unsubstituted or substituted as with halogen or another hydroxy radical. Others of the glycols which I can use are ethylene glycol, 2,3-butanediol and ether polyalkylene glycols, for instance where the alkylene radical contains 2 to 4 carbon atoms such as diethylene glycol and dipropylene glycol.
• Example IV of this patent a polymer allegedly having the following formula was produced by heating in the presence of water the product from the reaction of 2 moles of 2-methyl-1,3-pentanediol and 1 mole of tetraisopropyl titanate.
• n is a number greater than 1. Also, from this patent it is apparent that the reaction of the glycol and the titanium ester can be conducted in the presence of inert solvents, e.g. cyclohexane, n-heptane, benzene, etc.
• inert solvents e.g. cyclohexane, n-heptane, benzene, etc.
• R is the hydrocarbon radical of an original ester group and Y is the glycol hydrocarbon radical or residue, that is the glycol minus two essential hydroxy radicals.
• Y is the glycol hydrocarbon radical or residue, that is the glycol minus two essential hydroxy radicals. This structure might also be represented as polymeric structure was proposed.
• the base oil-compatible-titanium compounds I employ can be either monomeric, polymeric or mixed monomers and polymers. These materials can be produced through reaction, with or without heating, of about /2 to 4 moles of glycol with each mole of titanium tetraester, preferably about 2 to 4 moles of glycol per mole of titanium tetraester.
• the first product obtained can be employed as such or polymerized through heating or through water addition and heating with there being no particular critical limitation on either, except, of course, the temperature should not be so high as to decompose the desired reaction products. Ordinarily, the polymerization temperature will be above 25 C. :and preferably at least about 40 C.
• the structure of my additive agents might be defined as the base oil-compatible materials of the following formula wherein A is hydrogen, a hydrocarbon radical of a titanium tetraester, or B; and B is a glycol hydrocarbon radical containing a glycol hydroxy group.
• A is hydrogen, a hydrocarbon radical of a titanium tetraester, or B; and B is a glycol hydrocarbon radical containing a glycol hydroxy group.
• B is a glycol hydrocarbon radical containing a glycol hydroxy group.
• product (a) By infrared analysis, product (a) showed a strong absorption peak at 3 microns which is characteristic of a hydroxyl group. The intensity of the peak indicated a hydroxyl number of about 460. The hydroxyl groups apparently were derived by removal of unchelated glycol residues from the OGT-41 in the presence of water. By infrared neither product (12) nor (0) exhibited a hydroxyl number and these products appeared to be similar.
• my extreme pressure agents may vary from liquid to solid as long as they are compatible with the base oil.
• the molecular weight will be from about 800 to 3000 and preferably about 1000 to 1800, but the molecular weight may even be as high as 5,000 to 15,000 or 20,000 or more.
• the low molecular weight polymer additives frequently have viscosities at 100 F. ranging from about 0.575 to 0.85 cs. on the basis of 1 gram in 40 grams of toluene.
• My compositions contain suflicient of the titanium additive agent to increase materially the load carrying capacity of the base oil.
• the final lube composition will contain from about 0.001 to weight percent of the additive agent and I prefer about 0.1 to 2%. More than 5% could be used but there does not appear to be any necessity for this.
• the actual amount of agent employed may be dependent upon the degree of improvement desired and upon factors such as the character of the base oil and the other materials which may be added to or be present in the lubricant composition. For instance, one specification now of interest requires that the lubricant carry at least 3000 lbs.
• the degree of improvement in the load carrying properties of my lubricating oils, particularly synthetic oils such as the diester oils, afforded by incorporation of my titanium additives can be materially enhanced by providing in the composition a small but effective amount of a free, base oil-compatible dibasic acid.
• the compatible acids I use have molecular weights of up to about 600 which includes for instance monomer and dimer acids.
• the dibasic acid could be present when the lubricant contains more than about 0.1 weight percent of titanium should it be considered desirable or convenient.
• the free d.basic acid is about 0.01 to 0.1 weight per.- cent of the composition, and generally there seems to -be little if any benefit to be derived from using more than about 1% of the acid when it is added primarily to enhance the effectiveness of the titanium additive.
• the dibasic acids have been found to be useful along with my titanium additives the same result has not been obtained by incorporation of the monobasic acid, decanoic acid, or the half ester prepared from 2-ethylhexanol and sebacic acid.
• the agent may be as high as about of such a concentrate but normally the concentrate would contain about 15 to 60% additive.
• My additive monomers and the polymers made by heating in the presence of water can be blended with the base oil at room temperature but slight heating is preferred when blending this polymer. Polymers made by heating the monomers in the absence of water seem more difficult to blend and'temperatures of at least about 150 F. are generally employed during blending of these materials.
• My compositions can also contain additional agents such as anti-oxidants, anti-foaming additives, corrosion inhibitors, V.I. improvers, other extreme pressure agents, thickener-s and other agents added to give desired properties. However, certain agents may decrease the effectiveness of my titanium additives, and this has been found to be the case in instances when my composition contained tricresylphosphate and the OGT-41 polymer. the titanium additives of this invention exhibit anti-foaming activity.
• the base oils of my compositions are the mineral or .synthetic oils of lubricating viscosity.
• the synthetic oils consist essentially of carbon, hydrogen and oxygen, with or without silicon.
• Various of these lubricating materials have been described in the literature and generall their viscosity ranges from the light to heavy oils e.g. about 50 SUS at F. to 250 SUS at 210 F. and preferably 30 to SUS at 210 F.
• Included among the preferred synthetic lubricants are, for example, the polyalkylene glycols prepared from alcohols and alkylene oxides. A number of these oils are available as Ucons prepared from aliphatic alcohols and propylene oxide and having molecular weights of about 400 to about 3000.
• oils containing silicon include the polysiloxanes of lubricating viscosity, particularly the polymethyl, polyethyl and polyphenyl siloxanes, for instance of 200 to 1000 or more molecular weight.
• the esters are made from alcohols and either monoor polycarboxylic acids.
• dicarboxylic acids employed are those of 2 to 12 carbon atoms, particularly the aliphatic acids such as adipic, azelaic, suberic, alkenyl succinic, sebacic, etc.
• Preferred monocarboxylic acids are those of 8 to 24 carbon atoms ally contain less than about 20 carbon atoms and are generally aliphatic, such as the butyl, hexyl, 2-ethylhexyl and dodecyl alcohols.
• the alcohols can also be polyfunctional materials, such as glycols, and included among the glycols are the ether glycols.
• Various ester base oils are disclosed in United States Patents Nos. 2,499,983; 2,499,984; 2,575,195; 2,575,196; 2,703,811; 2,705,724 and 2,723,286.
• my preferred lubricating base oils are synthetic and consist essentially of carbon, hydrogen and oxygen with or without silicon, i.e.
• these oils may be substituted with other elements such as halogens, e.g. chlorine and fluorine.
• oils falling within the above classes are ethyl palmitate, ethyl stearate, di-(2- ethylhexyl) sebacate, ethylene glycol di-laurate, di-(2- ethylhexyl)phthalate, polymethyl siloxane of 149 SUS viscosity at 210 F., l-naphthyl cetyl ether, dicetyl ether, polypropylene glycol (and monoand diethers) (m.w.
• My monomer additives can be dissolved in a silicone oil; however, difliculty has been experienced in this respect when using the polymers.
• the polymer so formed will remain compatible with the silicone oil even when the concentrate is combined with additional base oil to prepare the lubricant.
• EXAMPLE III 773 grams of OGT-4l were placed in a 6-liter beaker. Four liters of deionized water were poured in with vigorous stirring by hand. A milky, yellow suspension formed. The mixture was heated and stirred. After about 5 minutes the temperature reached 28 C. and a white, tacky precipitate formed. After a total of 30 minutes when the temperature reached 55 C. the product took on a curdy appearance. At 65 C. there were three components present; a White, heavy, tacky precipitate; a clear solution and a yellow, only curdy material. The desired product (the White, heavy, tacky precipitate) was separated by decantation and filtration. The solid on filter paper was left in air overnight and then was stored in a desiccator for 20 hours. 134 grams of product were obtained and the product analyzed 25.6 Weight percent ash, which is equivalent (by calculation) to 15.3 weight percent titanium.
• An additive concentrate was formed by mixing 819 grams of the crude polymer with 800 grams of Plexol 201 and heating the mixture at 135 C. for 15 minutes.
• the resulting additive concentrate analyzed:
• EXAMPLE VI 100 grams of OGT-41 were mixed with 200 grams of water. The mixture was heated at 200 F. for 1 hour and then filtered. The filtered solid product was washed with 200 grams of hot water and then air dried for 24 hours. The dried product analyzed:
• EXAMPLE VIII A polymer was made by heating 100 grams of OGT-2l to 250 C. and holding this temperature for 5 minutes. It was more difficult to dissolve this polymer in Plexol 201 than the preferred polymers formed in the presence of water. At 350 F., 150 ml. of Plexol 201 were required to dissolve /2 gram of the polymer of this example.
• EXAMPLE X 2640 grams of polymers were prepared by combining three separate products, each obtained according to the following procedure. 7.2 parts of OGT-41 were mixed with stirring with 6 parts of water. The mixture was heated about minutes at 180 F. and it then stood overnight. A clear supernatant organic liquid and the water layer which had been formed were decanted from the resulting polymer. Nine parts of water were then added to the polymer and after heating and stirring for 30 minutes at 180 F. the mixture was. allowed to settle for 16 hours. The liquid phases were decanted and the polymer transferred to filter paper and air dried for 24 hours at 25 C.
• EXAMPLE XI An additional amount of polymer was prepared by the method of Example X and the products were combined to provide 2920 grams of air dried polymer. The polymer was then blended with 4735 grams of Plexol 201 to give an additional concentrate. Blending was accomplished by heating the titanium polymer in the Plexol 201 for 30 minutes at 160 F. and then filtering through paper. This concentrate analyzed:
• EXAMPLE XII 2000 grams of OGT2.21 were mixed while stirring with 4000 grams of water. The mixture was heated and held at 75 C. for 40 minutes. The aqueous and organic liquid layers were decanted from the polymer which had been formed and the crude polymer analyzed 16.1 weight percent titanium.
• EXAMPLE XIII 2000 grams of OGT-4l were mixed while stirring with 6000 grams of water. The mixture was heated and held 12 at 60 C. for about 16.65 hours. The aqueous and organic liquid layers were decanted from the polymer which had been formed and the polymer was air dried for 24 hours at 25 C. The resulting material analyzed:
• EXAMPLE XIV Ten liters of OGT41 were placed in a 40-liter stainless steel beaker. To this were added 30 liters of distilled water with agitation, and the mixture was heated at C. for three hours with stirring. The agitation and application of heat were stopped, and the contents of the beaker were allowed to cool to 25 C. At this point the butanol solvent and water (liquid layer) were decanted from the white precipitate of polymer. Thirty liters of distilled water were added and the temperature was increased to 80 C. with good agitation. The application of heat was stopped and the product was allowed to settle for four hours. Then water and solvent were decanted, and the polymer was dried for 60 hours at room temperature (25 C.) at about 30% relative humidity. The yield of air dried titanium polymer was about 38%. Analysis of the polymer was:
• EXAMPLE XV 164 pounds of OGT-41 were weighed into a stainless steel Pfaudler kettle. While stirring vigorously, 210 pounds of tap water were added. The stirred mixture of water and precipitated polymer was heated to F. over a twenty-minute period. When the mixture reached 170 F., the agitation was stopped, and the mixture was allowed to settle 1 hour. The upper organic layer and water were siphoned off the wet polymeric white solid. A second charge of tap water, 210 pounds, was added to the kettle, while agitating vigorously, and the mixture was heated to 170 F. The agitation was stopped, and the mixture was allowed to settle two hours.
• compositions 1 through 5 fall within the present invention while composition 6 not containing my additive is included for comparative purposes to show the improvement in load carrying capacity afforded by my titanium additive agents.
• a diethylhexyl sebacate oil having a kinematic viscosity at 100 F. of 12.3 centistokes, a viscosity index of 154, a pour point of below 80 F. and acid number of 0.12.
• 3 D.C.F. 200-60000 is a methyl silicone polymer having a viscosity of 60,000 cs. at C. and is an anti-foaming agent.
• compositions l to 5 frequently gave load carrying ratings of 5600+ on the Ryder test machine. As 5600 is the capacity of this machine, such readings do not, of course, indicate the ultimate load carrying capacity of the lubricant tested.
• the extreme pressure characteristics of these compositions are vastly improved over a similar synthetic lube oil composition containing no titanium additive where the composition had a rating on the Ryder machine of only about 2100 pounds, see composition 6 of Table II.
• a tentative proposed military specification requires a minimum Ryder rating of 3000 pounds which illustrates an inadequacy of the base oil composition not containing my titanium additive.
• composition weight percent:
• Emolein 2958 1 balance balance balance balance balance balance balance balance balance balance balance balance balance balance Di-2-ethylhexyl adipate 2 balance balance Phenot azine 0.. 0.5 0.5 0.5 0. 0.5
• the propylene oxide was flashed OE and the ht i igir ih t liiiiii Balance product analyzed: Acid No. ASTM-D974, .05; viscosity g g gfi gigjgg g g 96 40 at 210 F. centistokes 74.00.
• the resulting composition containing the ester thickgF ener and my titanium additive had a viscosity at 210 F.
• Tricresylphosphate t d 1 d a r ca acit 3440 is a widely used extreme pressure agent.
• sufliof be m a of grease (ionsls'tency' A grease of good coior body of a synthetic base oil and a mineral lubricating oil.
• load carryingcilpaclty can be made by aqdmg 10 Weigh;
• These blends can contain any desired amounts of the 2 3 1 gi g fi gf g gf g g gg Zg E EZ EZ: separate oils, as an example it might be desirable to use P y p a blend having as little as about 1 to 10 volume percent of -such g canhal-so g mineral lubn' of the synthetic oil
• the ester five 6 tested l g Tlmkzn $882k? gga gg thickener was prepared by charging to a SO-hter flask for ours Poun equipped with a metal paddle, stlrrer, az eotrope trap and '-P-
• the cup and block were bnght and pohshed and the polypropylene glycol 150, 7,000 grams of xylene and absence of ridging evidenced a lack of surface fatigue.
• composition weight percent:
• Base mineral oil contained 72 volume percent of 600 SUS at 100 F. solvent treated Mid-Continent neutral oil and 28 volume percent of 200 SUS at 100 F. solvent treated Mid-Continent neutral oil; the blend has a viscosity of about 450 SUS at 100 F.
• the Ryder gear rating was about 4900 pounds.
• the presence of the compatible dibasic acid in the mineral oil base gave some improvement in load carrying properties of the oil containing my titanium additive in an amount to afford about 0.03 percent titanium.
• a composition consisting essentially of a base oil of lubricating viscosity, a suflicient amount to enhance the load carrying capacity of an additive material selected from the group consisting of base oil-compatible products formed by the reaction of a titanium tetraester with a glycol-containing from 2 to about 24 carbon atoms, said titanium tetraester and glycol reacting in the ratio of about A to 4 moles of glycol to each mole of titanium tetraester, and the base oil-compatible polymers thereof, and an amount of a base oil-compatible dibasic acid sufficient to provide increased load carrying capacity to the composition.
• an additive material selected from the group consisting of base oil-compatible products formed by the reaction of a titanium tetraester with a glycol-containing from 2 to about 24 carbon atoms, said titanium tetraester and glycol reacting in the ratio of about A to 4 moles of glycol to each mole of titanium tetraester, and the base oil-compatible polymers thereof, and an
• composition of claim 1 in which the glycol is a 1,3-diol.
• composition of claim 1 in which the titanium additive material is about 0.1 to 2 weight percent of the composition is about 0.1 to 2 weight percent of the composition.
• composition of claim 1 in which the titanium additive material is a titanium tetraester-glycol polymer formed by heating in the presence of water.
• composition of claim 1 in which the titanium additive is in an amount to provide up to about 0.1 weight percent of titanium and in which there is present about 0.005 to 1.0 weight percent of the dibasic acid.
• composition of claim 1 in which the base oil is a diester is a diester.
• composition of claim 6 in which the titanium content is up to about 0.05% by weight of the composition and the dibasic acid is about 0.01-0.1% by weight of the composition.
• composition of claim 6 in which the dibasic acid has 2-12 carbon atoms.
• composition of claim 8 in which the reaction is with about 2 to 4 moles of a glycol containing about 18' 5l2 carbon atoms to each mole of titanium tetraester, and in which the titanium content is up to about 0.1% by weight of the composition and the dibasic acid is about 0.01-0.1% by weight of the composition.
• composition of claim 9 in which the titanium content is up to about 0.05% by weight of the composition and the dibasic acid has the formula COOH(CH COOl-l Where n is a number from 4 to 8.
• composition of claim 10 where the glycol is a 1,3-diol.
• composition of claim 11 where the base oil is di-(2-ethylhexyl)-sebacate.
• a composition consisting essentially of a diester synthetic organic base oil of lubricating viscosity and a sufiicient amount to enhance the load carrying properties of an additive material selected from the group consisting of base oil-compatible products formed by the reaction of a titanium tetraester with a glycol containing from about 5 to 12 carbon atoms, said titanium tetraester and glycol reacting in the ratio of about 2 to 4 moles of glycol to each mole of titanium tetraester, and the base oil-compatible polymers thereof, and an amount of a base oil-compatible dibasic acid suflicient to provide increased load carrying capacity to the composition.
• an additive material selected from the group consisting of base oil-compatible products formed by the reaction of a titanium tetraester with a glycol containing from about 5 to 12 carbon atoms, said titanium tetraester and glycol reacting in the ratio of about 2 to 4 moles of glycol to each mole of titanium tetraester, and the base oil
• composition of claim 13 in which the titanium additive material is a titanium tetraester-glycol polymer formed by heating in the presence of Water.
• composition of claim 13 in which the titanium additive is in an amount to provide up to about 0.1 weight percent of titanium and in which there is present about 0.005 to 1.0 Weight percent of the dibasic acid.
• a composition consisting essentially of a diester synthetic organic base oil of lubricating viscosity having added thereto a sufficient amount to enhance the loadcarrying properties of a base oil-compatible dibasic acid in the amount of about 0.01 to 0.1% by weight of the total composition and an additive material selected from the group consisting of base oil-compatible products formed by the reaction of a titanium tetraester with a glylcol containing from about 5 to 12 carbon atoms said titanium tetraester and glycol reacting in the ratio of about 2 to 4 moles of glycol to each mole of titanium tetraester, and the base oil compatible polymers thereof, in an amount sufiicient to enhance the load-carrying capacity and to supply up to about 0.1% by weight of titanium to the total composition.
• a lubricating composition consisting essentially of di-(Z-ethyhexyDsebacate as the base oil, about 0.1 to 2 weight percent of a base oil-compatible, additive formed by the reaction of a titanium tetraester with 2-ethyl-1,3- hexanediol, said titanium tetraester and diol reacting in the ratio of about 4 moles of diol to each mole of titanium tetraester, said additive being sufficient to supply up to about 0.1% by weight of titanium to the total composition and about 0.01 to 0.1 weight percent of sebacic acid.
• a lubricating composition consisting essentially of di-(Z-ethylhexyl) sebacate as the base oil, about 0.1 to 2 weight percent of a base oil-compatible, additive formed by reacting a titanium tetraester with 2-ethyl-1,3-hexanediol, said titanium tetraester and diol reacting in the ratio of about 4 moles of diol to each mole of titanium tetraester, and then heating the product of this reaction in the presence of water, said additive being suflicient to supply up to about 0.1% by weight of .titanium to the total composition and about 0.01 to 0.1 weight percent of sebacic acid.

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• Engineering & Computer Science (AREA)
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• 0
  • NL NL216503D patent/NL216503A/xx unknown
  • NL NL216504D patent/NL216504A/xx unknown
• 1957
  • 1957-03-21 US US647511A patent/US2960469A/en not_active Expired - Lifetime
  • 1957-04-18 DE DES53202A patent/DE1121259B/de active Pending
  • 1957-04-18 DE DES53203A patent/DE1112601B/de active Pending
  • 1957-04-18 NL NL216503A patent/NL111499C/xx active
  • 1957-04-19 FR FR1189913D patent/FR1189913A/fr not_active Expired
  • 1957-04-19 FR FR1186979D patent/FR1186979A/fr not_active Expired
  • 1957-04-23 GB GB12905/57A patent/GB866053A/en not_active Expired

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