US2604449A - Greases and compounds for making same and other compositions - Google Patents

Greases and compounds for making same and other compositions Download PDF

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Publication number
US2604449A
US2604449A US80328A US8032849A US2604449A US 2604449 A US2604449 A US 2604449A US 80328 A US80328 A US 80328A US 8032849 A US8032849 A US 8032849A US 2604449 A US2604449 A US 2604449A
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acid
grease
batch
greases
astm
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US80328A
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William C Bryant
Giordano Anthony
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Swan Finch Oil Corp
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Swan Finch Oil Corp
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M5/00—Solid or semi-solid compositions containing as the essential lubricating ingredient mineral lubricating oils or fatty oils and their use
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/14—Synthetic waxes, e.g. polythene waxes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/17—Fisher Tropsch reaction products
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/12—Partial amides of polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/06—Groups 3 or 13
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • The, principal object. offthe'ipresentinvention accordingly, .is "tojproduce. greases'arid other compounds prepared fi'om. .sal'tsdfiam'ic' acids shall overcome atleas't sor'netbith'ese disadvam tages and which shall have vsuperior characteristics to those found imthefiitherto known greases mentioned above.
  • Another' object of the inventtion is to provideiasuitable: base for produc-- ing such greases.
  • Anotherv object of the invention is to provide a series of'new'and useful compounds consisting of amic-'acid.s, derivatives an omp ndsthereet.
  • v -'I -he inventiom accordingly comprisesjhe evei products, Ithe ispecifics embodim-ents-.-.ot whichgare described hereinafter by way x0 2:e:gazrrpl'eand in accordance with which we now prefer to practice the invention.
  • the composition is smooth and somewhat thickend with respet to the cylifider bil methylene 'groups.havinga'rcarborr'chain ieitgth pure and we prefer to use such compounds in making up our greases and other compounds in order to avoid the difficulties encountered in the use of natural fats and fatty acids as heretofore employed.
  • the salts of amic acid prepared'by us in accordance with our invention include the following:
  • M is an alkaline earthmetal
  • R, R1 and R'z'are' as above defined, and R3 is selected from the group consisting of hydrogen and an amic acid radical having the formula si o- 3;
  • R, R1 and R2 are as above defined, and R3 and Rrare each selected from the group consisting of hydrogen and an amic acid radical having the m R( 3I 1R2 5'
  • the substances prepared by us in accordance with our invention may be either condensations of a primary amine with a dibasic acid or they may be condensations of a secondary amine with a dibasic acid.
  • N-mono-lauryl adipamic acid preparedfrom a primaryamine
  • N-di-lauryl adipamic acid prepared'from a secondary amine. It is not necessary, of course, that the radicals, R1 and R2, as given in the above formulae, should be identical.
  • amines which may be either primary or secondary amines are the following:
  • w ere n. Brand 2 are ias hereinaboye dedi-palmitylamine and di-stearylamine. These amines, as procurable, may contain a mixture of amines, which will react and appear in the final product. Thus, lauryl amine may contain'small quantities of other amines such as octylamine, but we prefer to keep the quantity of such impurities limited to a small amount. 7
  • Test Data lheoretical Actual Water loss ercent H Acidity-calculated as oleic acid P. do 18%) l l tl ir/letltmg point- 'so' 1 rogen c 7-" Mean molecular weight 3 if: L258 7 Color l White Odor H .i. Bland v 2. N-mono-n-octyZ-sqbdcamic add.
  • Test Data Theoretical Actual I V I i r Test Data Theoretical Actual Water lossi'. ;..porcent; 2.49 2.44 Acidity-calculated as o vld. Water loss. 1 percent. 5.14 5.0 Melting pomt. 5 9 Aciditycalculatcd as oleic acid. do 84. 9 85. 23 Nitrogen .pcrcent l. 98 1. 92 Melting point 0 85. 7 Mean molecular weight 705 I 700 Nitrogen-.. .percent.. 4. 22 4.14 Colon. Crefim Mean molecular weight... 332 331 Odor Bland Color Cream Odor Spicy 12. N-mono-n-butyZ-azelar'imic acid 30 O l6.
  • the batch was rocesse exac y "s in simple 1 1 I ,7
  • the batch was processed exactly as in Ex- 0 ample 4..
  • the batch was processed exactly as Example 4.
  • Test Data Theoretical Actual Water loss -Per Cent 4. 90 5. 01 Acidity-calculated as oleic acid do 81. 7 81. 9 Melton point. 7 C 89. 0 Nitrogen .Per Cent.. 4.06 3. 94 Mean molecular weight 345 344 Color- White Odor- Bland 30. N -monopaZmityl-adipamic acid II II I HOC(CHi)4-C-N-C cHn "1 Parts Palmitylamine 245 (62.4%)
  • the batch was processed exactly as in Example 4.
  • Test Data Theoretical Actual Water loss -.percent 4.
  • 34 4. 50 Acxdity-calcula do 71. 0 71. 3 Melting point 76.2 Nitrogen perceut 3. 53 3. 50 Mean molecular weight 397 396 Color.
  • N-distearyZ-adipamic acid on) OHS opaque H 1 1 35m" as; iv-mme-eecyz' mazonamc ester HO-C-(CHa)4.-.N C1
  • Test Data Theoretical Actual wm 1q'ss, .-p ercerit 5.66 5. 71 Acidity-calculated as oleic acid 'do 94. O 94. 3 Melting point.-. C 40. 0 Nitrogen percent.. 4. 67 4. 64 Mean molecular weight. 300 299 Color--.” (Jream .Orinr Sp y 44. N-monomyristyl-itaconcmtic acid H -C-H Ti; fi I H-(i7C.l?'.C14 z7..
  • Test Data Theoretical 'iActual Water loss. percent 4. 8 5. 1 Acidity-calculated as oleic acid- 0.--. 79.0 79. 7 Melting point Q 59. 2 Nitrogen -percent.. 3. 92 3. 87 357 354 Cream v p y 46. N-mono stearyZ-itacmmmic acid, H-C-E I I O 11 CC -0--H I! H- C-I?'CnHa1 Parts Mono stearylamine 270 (67.5%)
  • the N -lauryl sebac amie acid and oil are added to a kettleand heated to about 400-440 F.
  • the sodium hydroxide'is'" dissolved'in three times its weight of water and is slowly added to the heated sebacamic acid and oil in thelkettle. Reaction commences.
  • the addition of the alkali solution is controlled so that the temperature is about 435 F. when all. of the alkali has been completely added; the grease iscooled to about 120 F. maximum without disturbing, that is, without raking, stirring or otherwise agitating it.
  • the grease is then milled that is, passed over rollers, kettle stirred, or passed through-a homogenizer or-milluntil the structure is substantially homog'eneous.
  • the batch was made exactly as in Example 47.
  • the finished grease had the following properties:
  • N-ZauryZ-barium sebacamate grease Per cent N -lauryl-s'ebacai'nic acid 11.44 Barium hydroxide octahydrate 4.28
  • the batch was made'exact'lyas in Example 47' except that crystals of alkali were used.
  • the finished grease had the following properties:
  • the batch was processed as in Example '47, except that the lime was made up as a 1:3 slurry in oil.
  • the finished grease had' the following
  • the batch was processed as in Example 50-.
  • the finished grease had the following properties:
  • the batch was. made exactly as in Example 47.
  • the finished grease had the following properties:
  • the batch was made as in Example 47.
  • the finished grease had the following properties:
  • N-oZegZ-lithium sebacamate grease I Per cent N-oleyl-sebacamic acid 10 Lithium hydroxide monohydrate .75 300/ 100 F. S. S. U. Tech. white oi1 89.2 5
  • the batch was made as in Example 47.
  • the finished grease had the following properties:
  • Example 47 The batch was made as Example 47.
  • the finished grease had the following properties: Penetration ASTM D-217-47T "'270 D./P. ASTM D-56642 360 F.
  • the batch was made as in'ExampleY47.
  • the finished grease had the following-properties:-
  • Example l 7 The batch was made as in Example l 7.
  • the finished grease had the following properties: Penetration ASTM D-217 l7'-1. L' 245 D./P. ASTM D-566-42 1 F 371
  • the grease of Example 60. was" dilutedfurther with Residual black oil 3500/l00 F. S. S. U. at room temperature so that the salt content in the formula was about 2.9%.
  • the properties of this composition were:
  • The. batch was made as in Example 47.
  • the finished grease had the following properties:
  • the batch was made as in Example 47.
  • the finished grease had the following properties:
  • the batch was made as in Example 47.
  • the finished grease had the following properties:
  • the batch was made as in Example 47.
  • the finished grease had the following properties:
  • the batch was made as, in Example 47.
  • the finished grease had theiollowing properties:
  • the batch was made as in Example 47.
  • the finished grease had the following properties:
  • the batch was made as in Example 47.
  • the finished grease had the following properties:
  • Viscosity (Gardiner Mobilometer at 77 F.) 1 1 100 10oo Po'ur point F -15 This test is made with'a series of disks numbered from 1 to 3 with arbitrary weights, the viscosity being meas- 7 ured by 'disk;movement through the material tested and being represented in seconds.
  • Gardner Mobilometer viscosity is designated as 1-100-1000 which represents #1 disk, 100 gm. weight, and 1000 seconds at 77 F. Gardner Mobilometer viscosities hereinafter referred to are simply designated similarly to the expression quoted above.
  • the batch was made as in Example 47. .
  • the finished grease had the following properties:
  • Thebatch was made as in Example 47.
  • the finished grease had the following properties:
  • the resultant grease had the following proper ties:
  • Example 47 The batch was made as in Example 47.
  • the resultant grease had the following properties: Viscosity (Gardner Mobil- 7 ometer at 77 F.) 2-50-(30 to 40) Water tolerance Chrysler 10% Heat stability test (Gardner The heat stability test indicated that the grease does not thin out rapidly as the tempera ture is elevated under ordinary operating conditions. 1
  • Aluminum-mofio-N-lauryl sebacamate grease 392 parts of the sodium salt of the N-lauryl sebacamic acid were dissolved in 1000 parts of water at room temperature. To this solution were added 80 parts of sodium hydroxide. When the above solution was homogeneous, it was heated to boiling, about 212 F. A solution made up of 171 parts of aluminum sulfate nonahydrate dissolved in 500 parts or water was slowly added to the first solution. Boiling was maintained and, after all of thesolution had been added, the boiling was continued for30 minutes. The salt which had risen to the top of the aqueous portion was separated from the aqueous portion by siphoning off the aqueous portion. Fresh water was added to the salt and reboiled. This separation and reboiling was co-ntinuedwith fresh wateruntil the aqueous portion was neutral to phenolphthalein. The salt was then dried and powdered.
  • a mixture of the aluminum salt and oil to make the grease was prepared in the following manner: 1
  • the finished grease had the following properties:
  • a mixture of the aluminum salt and oil to make the grease was prepared in the following manner:
  • reaction mixture Since there were-three (3) parts of sodium salt in excess, the reaction mixture was alkaline to phenolphthalein.
  • the aluminum salt was purified by several washings of boiling water, until the washings were neutral to phenolphthalein. The salt was. then dried and powdered. 1
  • a mixture of the-aluminum salt and oil to make the grease was prepared inthe following manner:
  • the finished grease had the following lproperties: i
  • the alkaline earth metal salts of the various amic acids may be made in a similar manner to the aluminum'salts made above, namely, by combining the alkali metal salt of the amic acid in water solution with the appropriate alkaline earth chloride or other water-soluble alkaline earth salt. Purification is accomplished in the same manner as stated for the aluminum salts above.
  • MIXEDAMIC' ACIDS GREASE?) TI-IEREFROM Y a It has been found in accordance with our invention that by using mixtures of one or more difierent salts of amic acids, we may vary the properties thereof and of the greases therefrom advantageously.
  • exceptional water tolerance such as but without limitation, a salt of N-stearyl sebacamic acid
  • rust protection may be improved by using a salt of N-oleyl sebacamic acid
  • shear stability may be improved by using a salt of N- lauryl sebacamic acid
  • dropping point may be improved by using a salt of N-octyl sebacamic acid.
  • amic acid was made in the same way as provided in Example 4. V e
  • the amic acid had the following properties:
  • the amic acid was made in the same way as provided in Example 4. V
  • the amic acid had the following properties:
  • the finished grease had the following properties:
  • the properties represent a combination of properties resulting from the .use of the mixture of amines in the formation of the grease base, which accordingly is a mixture of salts oi the various amic acids made from such amines.
  • Lubricating greases made with compounds in accordance with our invention are superior to the greases made with the natural fatty materials in that the dropping, points of the greases made in "accordance with our invention are from 50.--75 F. higher than the best natural fat greases of. equivalent gelator content.
  • the amic acid compound greases, because of the polarity of the gelator are rust preventivesand will actually displace water from metal surfaces. and will resist water after the surface has once been treated with the lubricant.
  • natural fatty materials are mixtures of substances, some of which do not form greases. These non-grease forming substances are present in varying amounts and accordingly change the, greases. In the greases of our invention all ingredients employed. form greases and there is substantially no non-grease forming material.
  • a mixture containing a substantial proportion of a gelation agent and a petroleum lubricant said gelation agent being selected from the group consisting of the alkali metal salt of an amic acid having the formula and a polyvalent metal salt of said amic acid, where R is selected from the group consisting of methylene groups having a carbon chain length of 1 to 8 carbon atoms and the group R1 is an aliphatic-radical of a carbon chain length of 4 to 18 carbon atoms,'and R2 is selected from the group consisting of hydrogen and an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms.
  • a mixture containing a substantial proportionof a gelation agent and a petroleum lubricant said gelation agent being a compound having the formula v 0 Ill 0 where M is an alkaline earth metal R. is selected from the group consisting of methylene groups having a carbon chain'of -1 to 8. carbon atoms and the group .i
  • R2 is an aliphatic radical. of a carbon chain length of 4 to 18 carbon atomsgand R3 is selectedfrom the group consisting of hydrogen. and an amic acid radical having the formula O O i 4.
  • a'mlxture containing a substantial proportion of a gelation" agent and a petroleum lubricant said gelation agent being a compound having the formula where R iss elected from the group consisting of methylene groups having a carbon chain of 1 to 8 carbon atoms andthe group I I R1 is an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms; R: is selected from the group consisting of hydrogen and an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms.
  • R3 and R4 are each selected from the group consisting of hydrogen and an amic acid radical having the formula 5.
  • a grease having about 0.5% to 30% grease base of the total weight of the grease, said grease base being selected from the group consisting of an alkali metal salt and a polyvalent metal salt of an amic acid having theformula where R is selected from the group consisting of methylene groups having a carbon chain length of 1 to 8 carbon'atoms and the-group.
  • R1 is an aliphatic radical of a carbon chain length the group consisting of an'alkali metal salt and a polyvalent metal salt of an amic acid having the formula g t a i HOCR-CN-Rz v where R is selected from the group consisting of methylene groups having a carbon chain length of 1 to 8 carbon atoms and the group i R1 is an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms, and R2 is selected from the group consisting of hydrogen and an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms, and the remainder of the grease being composed principally of petroleum oil.
  • a grease composed of about 0.5 to 30% of N-lauryl.alkali metal sebacamate and the remainder being composed substantially of mineral oil.
  • a grease composed of about to 13% of N-laurylalkaline earth. metal sebacamate and the remainder being composed substantially of mineral oil.
  • a grease composed of about 1 to 10% of N- oleylalkali metal sebacamate and the remainder being composed substantially of mineral oil.
  • a grease "composed of; about 10% of N- palmityl.alkali' metal sebacamate and the remainder being composed substantially of mineral oil.
  • a grease composed of about 6% of N- laurylalkali metal azelaamate, and the remainder being composed substantially of mineral oil.
  • a grease composed of about 10% of aluminum di-N-lauryl sebacamate and the remainder being composed substantially of mineral oill 13.
  • a composition containing a substantial pro- 0 II o R1 is an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms, and R is selected from the group consisting of hydrogen and an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms.
  • a composition containing a substantial proportion of a gelation agent and a petroleum lubricant said gelation agent being a mixture of at least two substances selected from the group consisting of an amic acid salt having the formula x-oi-R-t-1L' Rz where X is an alkali metal, R is selected from the group consistin of methylene groups having a carbon chain length 011 to 8 carbon atoms and the group 7 v REFERENCES CITED.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Description

Patented July 22, 1952 :..poration;of:New.-York 'NoTDravvIing; Application March 8, 1949.
"'sli'allNo. 80,328
' "cially' produced are madeby the addition of soap or'a mixture ofsoa'ps tolubri'cating *oils -and/or other-petroleum" fractions. The soap'or' soaps serve to produce" gelz'itio'n 'iof tire-mixture. The g'elledmassrmay-vary in consistency from ja stilid' 'bfickto a-viscous oil of 'a slightly greater vicosity than the original, oil. The. usual greases sodas'o'a'ps metro-reunion: or other petroleum substance; Instead ofsddamotassiumpr lithium soaps'may *be usedalone'pr incombinaitionwith -calcium-,"-barium-or*strontium soaps; "These calcium, sodaand potassium greases "have "wellk ncwn-disadvantages. FOr"BXaII1p1e,.lWhI1TIISiIIg sodium or potassiumtsoaps, ,the resultant greases are not resistant twwater 'and, where used in wet places, form: emulsions which run off the parts being lubricated. The lime soap. grease and the soda-arid-potassiumsoap "greases have poor operating qualitiesat'low temperature, each producing highstarting torques, at such low temperatures,. for.example, at -20 F. On the other handr when the calcium greases are heated up to: theimeltin'e point; "the "water 'o'f; ge1ation,the so-c'alled 'tie water; i's'boile'd on" if thetempe'ratuxeszremainswatrsuchzpoint for'..anyiconsiderable etime; Thereafter; .vzlienthe 4g ease lcools; Lathe soap tends:toirseparaterfrcmz thei oilisinc'e; it lacks .the'-"iit'iev.iwater; ':Whehtthezsodium:andzpotasslum. greasesaretheatediup'zand cooled; the itend toiset'to aimu'ch heavier -ma;SSI WhiChI1i$ unstable to shearingforees; vThe:rcialcium:greases, fur-ther- :more,-have relativeiyzicvwdroppingpoints -"C*alcium and sodium potassiumL'greaseslhaVelittle rust preventive-action. Thebari-um and strontium g-reasesrrequire at leasthalfragain as much "soap-per equivalent-gelling-eniciency'as the-soadinmv greases. Barium and strontium rgreases J-are water resistant-and "resist "temperaturesup mnerronr iatsandiattyracids whicli have-mdn :55 still fluid,
alizfllaimsi Cl. 252-335) siderable variation-in their constitution as procureable on the market from time to time and hence cause considerable variation in the greases producedtherefrom.
The, principal object. offthe'ipresentinvention, accordingly, .is "tojproduce. greases'arid other compounds prepared fi'om. .sal'tsdfiam'ic' acids shall overcome atleas't sor'netbith'ese disadvam tages and which shall have vsuperior characteristics to those found imthefiitherto known greases mentioned above. Another' object of the inventtion is to provideiasuitable: base for produc-- ing such greases. Anotherv object of the invention is to provide a series of'new'and useful compounds consisting of amic-'acid.s, derivatives an omp ndsthereet. v -'I -he inventiomaccordingly comprisesjhe evei products, Ithe ispecifics embodim-ents-.-.ot whichgare described hereinafter by way x0 2:e:gazrrpl'eand in accordance with which we now prefer to practice the invention.
We have found in accordance with our inventionthat a 'cemposi tion--eontainingaepropertion -o'f rralkali metal 'saltoma-polyvalentimetalisalt cf 'amicacidhaving the formula' (A), go o n v V leaa s m. v where"RissIectedfrontthe"groupxconsfstirigifl Reels. .an aliphatic eradical a-.'ca1ibon'..;chain length at 4Lto I8.caibonatomasazidiRaisseleted fro'mrtherlgroup -eonsis'ting. of .hmogenanaan aliphatic. radical. ofla carbon uchaa'nllen gthrof L .4 3501 I8 carbonsatoms mixedwwith: asproportiomf petroleum substance such as various petroleum oils,;. petrolatumsor likersubstanees producesiiseA "fiil; lubricating -characteristics. Wl:ien: the.. salt dfiamic acidi longrease base) giyenmmeio mma jijs' presenti'irrftheapioportin labout letorabout iraaomnegrease, ifiLiEormsea-smooths semisst ilid mass at room temperature. Compounds containing more than 17% range upwardly to an'eirtremely hardeons'istency: WhesaIiT-O'f amic acid (or grease base)::may be ccntainedzin other pro portions, say, from 0.5%"2110 30% of the 0011113681?- tion for varying purposes. With. 0.5% composition using affiuid petroleum. oil. such as cylinder oil, the composition is smooth and somewhat thickend with respet to the cylifider bil methylene 'groups.havinga'rcarborr'chain ieitgth pure and we prefer to use such compounds in making up our greases and other compounds in order to avoid the difficulties encountered in the use of natural fats and fatty acids as heretofore employed. The salts of amic acid prepared'by us in accordance with our invention include the following:
where M is an alkaline earthmetal; R, R1 and R'z'are' as above defined, and R3 is selected from the group consisting of hydrogen and an amic acid radical having the formula si o- 3;
where R, R1 and R2 are as above defined, and R3 and Rrare each selected from the group consisting of hydrogen and an amic acid radical having the m R( 3I 1R2 5' The substances prepared by us in accordance with our invention may be either condensations of a primary amine with a dibasic acid or they may be condensations of a secondary amine with a dibasic acid. For example but without limitation, as indicated below, wehave produced in accordance with our invention, N-mono-lauryl adipamic acid preparedfrom a primaryamine, and N-di-lauryl adipamic acid prepared'from a secondary amine. It is not necessary, of course, that the radicals, R1 and R2, as given in the above formulae, should be identical. They may be the same or they may be radicals of different chain lengths within the definitions given therefor. Thus; w -recognize cojmp-ounds such as N-laurylpalmityl-adipamlc acid andsimilar substituted acids where R1 and Rzare of different chain lengths as falling 'under the formulae above given." I The amic acids ofiour'invention result from the condensation of an amine with adibasic acid in stoichiometrical' proportions so as to amidate only one of the available carboxyl groups in accordance with the following generaliequations:
1 J j 1 a. T. B TTH F 2 (dibasic acid) .(amine) fle t e es- (amic acid).
We may employ in accordance with our in vention the following dibasic acids falling under the above Formula E: Itaconic acid, adipic acid (hexanedioic acid), succinic acid (butanedioic acid), azelaic acid (nonanedioic acid), sebacic acid (decanedioic acid), and malonic acid (propanedioic acid), and others.
Illustrative of the amines which may be either primary or secondary amines are the following:
Mono n-butylamine, mono-n-hexylamine, monon-octylamine, mono-n-decylamine, mono-laurylamine, mono-myristylamine, mono -palmitylamine, mono-stearylamine, mono-linoleylamine,
mono-oleylamine, di-octylamine, di-laurylamine,
w ere n. Brand 2 are ias hereinaboye dedi-palmitylamine and di-stearylamine. These amines, as procurable, may contain a mixture of amines, which will react and appear in the final product. Thus, lauryl amine may contain'small quantities of other amines such as octylamine, but we prefer to keep the quantity of such impurities limited to a small amount. 7
The following are examplesillustrative of our invention of (I) Amic acids, (II) Salts of such acids and greases madetherefrom, and (III) Mixed amic acids and greases therefrom including processes for making each of Groups I, H and 111. It is to be understood that these'examples together with the examples of the dibasic acids and amines given above are illustrative and the invention'is not to be considered as limited thereto except as indicated in, the appended claims. r I r The molecular weights of the amic acids which are given below as theoretical are the molecular weights calculated from the reacting weights of the commercial ingredients which as heretofore stated may contain small amounts of impurities. To the extent that these impurities occur, the stated theoretical molecular weights of the compounds difier from the theoretical molecular weights of compounds of. purity.
V (I) AMIC ACIDS 1. N-mono-n -butyl-sebacamic acid 7 no-tt-ronort il r-oim Parts Mono-nebutylamine' '73 (26.4%) Sebaci c acid ;l 203 (73.6%)
Test Data lheoretical Actual Water loss ercent H Acidity-calculated as oleic acid P. do 18%) l l tl ir/letltmg point- 'so' 1 rogen c 7-" Mean molecular weight 3 if: L258 7 Color l White Odor H .i. Bland v 2. N-mono-n-octyZ-sqbdcamic add.
iMono-n-octylamine. 129.( 38.85%) Sebacic acid;.: 203 (61.15%)
The batch.was.processedwexactlyasforfEx- .-'The batch. was processed exactly as in Example 9. ample 3.- I r Test data 7 Theoretical Actual Test Data Theoretical Actual 5 Water loss -1 percent. 2. 69 2. 63 percent 5. 62 5. 51 Acidity-calculated as oleic acid do. 43.4 43.7 d0 93.3 93.7 Melting point. --C 87. 6 1 84. 3 Nitrogen. percent- 2. 15 2.12 Nitrogen ercent..- 4. 64 4. 59 Mean molecular weight 650 V r 645 Mean molecular weight 302 301 Colo Cream Color White Odor Bland 10 Odor Spicy "11. N-distearyZ-sebdcamic acid 5- m y -az ic acid f n I HO=HE(CH1)s H 31 Parts Parts sec. steaiy1amine 1- 521 (71.9%) qe 160 .7%) Sebacic acidhw; '203 (23.1%) Azelalcecld- 1 4.3%) The batchwas made exactly as in Example 9. The batch Was p ce sed exactly as in Example3;
Test Data Theoretical Actual I V I i r Test Data Theoretical Actual Water lossi'. ;..porcent; 2.49 2.44 Acidity-calculated as o vld. Water loss. 1 percent. 5.14 5.0 Melting pomt. 5 9 Aciditycalculatcd as oleic acid. do 84. 9 85. 23 Nitrogen .pcrcent l. 98 1. 92 Melting point 0 85. 7 Mean molecular weight 705 I 700 Nitrogen-.. .percent.. 4. 22 4.14 Colon. Crefim Mean molecular weight... 332 331 Odor Bland Color Cream Odor Spicy 12. N-mono-n-butyZ-azelar'imic acid 30 O l6. N-mono Zauryl-azelaamic (101d n o HO(CHz)7-CNC4HB HO-C(CHi)1-C C12 2s Parts Parts Mono-n-but lamine -'73' (27.8%)
Azelaic'acidf 1.90 (72 2% Monolaurylamine 188 9.8%) t1 EX A laic acid 190 (50.2%)
The batch was rocesse exac y "s in simple 1 1 I ,7 The batch was processed exactly as in Ex- 0 ample 4..
Test Data Theoretical Actual I Test Data Theoretical Actual Water 15158-1: .1jcrblit. 6.34 6.30 v Acidity-calculated as oleic acid. c lo I 115.0 115.4 'Water1oss; percent 43,8 Memng point-H c v 22 Ac1d1 ty-calculated as olcic acid" 7s, 3 7 5 Nitrogen percent 5. 72 5. 66 Melting pomt 2 Mean molecular Nitrogen 3.89 3.83 p mvMean molecular weight 3 0 3 9 Color Light v Brown Odor.-. Q 9 Spicy 13. N-mcmo-h-hexyl -azeladmicaacid, Q no yr styl-azeladmic acid .0 O H. O 11 g I [I H l O.- 2)1' -C\1Hz$ HO-C(C :)7-CNC14H:9 Parts Ij Parts Mono-n l'ie xylamlnenfl 10l(34.7%) 55 9 ri 1 e 215 (53.2%) Azelaic acid 190(65.3 Azelaw wd 190 (46.8%) The batch was processedrexactlylasiini Ex- The batch Was p cessed exactly as in Example I Z 1 a'znple Test Data Theoretical Actual Test Data I Theoretical Actual ercent- 6.19. 5.24 a r per eent-- 4.45 4.49 lllifi imm asol ic p do 104.0 103.7 Acldlty-e=ilculated as @1610 M111 72.8 73.1 Melting point. B 81.1 P .0. 88.6 Nitrogen; .percent.- 5. 07 5. 12 mogen percent. 3, 61 3, 55 Mean molecular 271 271 45 Mean molecular weigh 387 385 5 Color 'White F Cream om t.--
Spicy Bland 141-::N-jnonoeneoctyl-azelaiimic .acz'd .-m0fle m mi ra l m @1 :10; V H I V 0 0 I HO'.(U: (QHE)1.I CNVOBHH fwfiflfl f fQmflu I-- v Parts 1 '1; Parts Mond- -octylamine;. '1-30.( 1 ..7i%.) =Moniopalmltylamine 13 5 5 The batch was processed exactly as 'in Example 3.
Test Data Theoretical Actual Water loss per cent 5. 84 5. 92 Aciditycalculated as olcic acid 0.--- 97. 3 97. 7 'Melting point 105.0 Nitrogen per cent 4. 83 4. 77 Mean molecular weight 290 288. 5 Color White Odor Spicy 28. N=manolauryl adipamic acid H I l HOC (CH1)4- -CizEf2s Parts Laurylamine l88 (55,.9 Adipic acid 148 (44.1%)
The batch was processed exactly as Example 4.
Test Data Theoretical Actual Water loss Per Cent. 5. 3 5. 42 Acidity-calculated as oleic acid o- 88. 7 89. Melting point 96. 7 Nitrogen Per Cent 4. 40 4. 42 Mean molecular weight 318 310. 5 Color- White Odor- Spicy 29. N-monmnyristyl-adipamic acid I! ll HO-C-(CHDt-C-N-CML V x Parts Myi istylamine 215 (59.2% Adipic acid 148 (40.8
The batch was processed exactly asin Example 4.
Test Data Theoretical Actual Water loss -Per Cent 4. 90 5. 01 Acidity-calculated as oleic acid do 81. 7 81. 9 Melton point. 7 C 89. 0 Nitrogen .Per Cent.. 4.06 3. 94 Mean molecular weight 345 344 Color- White Odor- Bland 30. N -monopaZmityl-adipamic acid II II I HOC(CHi)4-C-N-C cHn "1 Parts Palmitylamine 245 (62.4%)
Adipio acid 148 (37.6%)
The batch was processed exactly as in Example 4.
Test Data Theoretical Actual Water loss percent 4. 58 4. 63 Acidity-calculatcd do.- 75. 2 75. 5 Melting point.. 0-. 82. 0 Nitrogen percent- 3.73 I 3.70 Mean molecular weight 375 373 Color White Odor Bland 31. N -momstearyl-adipamtc acid H 0 g H 1 .HO- (CH:)4CNC1aHa1 Parts Stearylamine' 270 (64.6%) Adipic acid c 1 43 (35.4%) The batch was processed exactly as in Example 7.
Test Data Theoretical Actual Water loss. .percent 4. 31 4. 41 Acidity-calculated as oleic acid .do 70. 5 70.7 Melting point C 81.4 Nitrogen percent 3. 50 3. 47 Mean molecular weight 400 399 Color Tan Odor Bland 32. N-monooleyZ-adzpamz'c acid 7 ll ll l l I HO-C(CHz)-i-CNClaHas Parts Oleylamine 267 (64.4%) Adipic acid 148 (35.6%) The batch was processed exactly as in Example 7.
Test Data Theoretical Actual Water loss -.percent 4. 34 4. 50 Acxdity-calcula do 71. 0 71. 3 Melting point 76.2 Nitrogen perceut 3. 53 3. 50 Mean molecular weight 397 396 Color. Opaque Amber .Odor Blend 33. N-diZaur'yZ-adipamic acid I H 0 Cufiza H0-'ooH-l)ro-N cnm.
Parts Sec. laurylamine 356 (70.65%) Adipic acid 148 (29.35
The batch was processed exactly as in Example 9;
was processed exactly. es; irrfiExample- 9.
1'4 1111c; batch-was processed exactlyasairr. amp1e36. v
36. N-mono-n butyl malonamicrester" .H I H c1H,-0-o'-oH o'-N cu1.
Since malonic acid is unstable in normal atmospheres-;-weused=malbriicester; a i a C:H;O C-(l. J-O-C1H:
as the source of malonic radical. Instead of water bein evolved, ethanolv is the reaction product.
Parts Mono-n-butylamine '73 (313%) ester .160 468.1%.) The-malonic ester was heated to '27 0 'F -'I-he mono-n-butylamine was added slowly and the temperature was perrmttedtoizise- 'toflaw-31o?F.. after all theamine had "been'added. After four (:4) .hours am i290-310 F., saponification equivalencyandweight loss indicatedthe end-of the re- D 11 'Saponiflcation"equi'valentcalcuiated*asoleie 1 Test Data Theoretical :actual 6 Test Data Theoretical Actual as E .3102 'Ethanolloss emnt-., mass?) 15:80
47.45: 41:16 calculated oleic I 88.3 p :3 Nitrogen; lperoentfi- 2:31 245 Mmmolecular-wei'ghL r. v i 595.. :593 5.170 Cnlnr Tan Odor 'Soapy Spicy I Am 11 whit lid. 35. N-distearyZ-adipamic acid on) OHS opaque H 1 1 35m" as; iv-mme-eecyz' mazonamc ester HO-C-(CHa)4.-.N=C1|Ha1 lO| H; t Parts sHa-Q G-lflliN-CmHu Sec.- stearylamine 521 (77.5%) a Adipic acid 148 (22.5%) 2 P ts ar The batch was processed? exactly as in Ex- Mona-.decylanflne 160 (50%) -mr MaIonic ester 160 (50 Test'rfate Thwwflfliilimmal The' batch wasprocessed.exaotl; usain Exarurle r 36, except the reaction time, which was four (4) W iter;loss "W""a"....u.W ..;'pe1'ceut.. .2. 69 .2. 78 hours. I v Acidity-calculatedasoleic'acidj do 43-.3- "-43.6 V .7 Melting point P0 97.8 1- Nitrogen. "percent" 2. 15 2. 05 V l gz u lf z 651 fg Test Data Theoretical Actual Odor pyao Y Y Ethanol loss percent; 'Sapouificatiou:equivalent-calmlated. as olelc.
1 Amorfifious opaque creaui'cbloredsolid.
- Parts Mono-laurylamine 188 (54%) Malonic esterfl 160 (46%) Jb'atch .was made exactly as-ifnEx-amnle38.
'De'stData Theoretical Actual ac1d percent Meauvmole'cula'r weight. Nitrogen; Appearan 1 Amorphous opaque creaurcoloredsolid.
I Parts Mono n-butylamine 73(36%) Itaconicacid (64%) The butylamlne and itaconic acid were added to a vessel together, and the temperature was slowly raised to 260 F. The amidation'began at 215 F. with copious evolution of water. The
temperature was maintained at 26.0=-280"-;E. until the reactionuwas complete, which was'evidenced .Water loss Acldi tycalculated as oleic ac1 15 by cessation of evolution or water, after forty (40) minutes. V
'Itaconic 'acld 130 (50%) The batch was made as in Example 0, except that the reaction time was one (1) hour.
The hatchwas processed as in Example 40, except that the reaction time was 80 minutes. I
. Theoretical Test Data Actual 6. 10 104; 36. 7 5. 11 271. Yellow Spicy Pai'ts The batch was made exactly as in Example 42.
Test Data Theoretical Actual wm 1q'ss, .-p ercerit 5.66 5. 71 Acidity-calculated as oleic acid 'do 94. O 94. 3 Melting point.-. C 40. 0 Nitrogen percent.. 4. 67 4. 64 Mean molecular weight. 300 299 Color--." (Jream .Orinr Sp y 44. N-monomyristyl-itaconcmtic acid H -C-H Ti; fi I H-(i7C.l?'.C14 z7..
. B H, s
Parts Myristylamine 215(62.3%) Itacon-ic acid (37.7%)
" The batch was made exactly as in Example 42.
Test Data Theoretical Actual Water loss. percent- 5. 22 5. 4o 'AciditY-calculated as oleic acid do 86. 2 86. 4 lVIelting pni'nf C 48. 7 Nitrogen .percent I 4. 28 4. 22 Mean molecular weight 327 326 Color" Cream Odor Spicy I 45. N-moino'paLmityZ-itdconcmic acid H-c-"H .4 C-OH I. H-C1'( mHaa I j Parts Mono palmitylamine 245(65.3%) Itaconic acid 130(34.7%)
The batch was made exactly as hi Example 42.
Test Data Theoretical 'iActual Water loss. percent 4. 8 5. 1 Acidity-calculated as oleic acid- 0.--. 79.0 79. 7 Melting point Q 59. 2 Nitrogen -percent.. 3. 92 3. 87 357 354 Cream v p y 46. N-mono stearyZ-itacmmmic acid, H-C-E I I O 11 CC -0--H I! H- C-I?'CnHa1 Parts Mono stearylamine 270 (67.5%)
Itaconic acid 13062.5
The'batch was processed'the same as in Example 42, except that the reaction time was two ('2') hours. V. i
Test Data Theoretical Actual Water loss percent 4. 4. 9 Acidity-calculated as oleic acid d 73. 8 74. 0 Melting point 68.6 Nitrogen 3.- 67 ,-3. 61 Mean molecular weight 381 Color Tan Odor Spicy 47.N-lauryl-sod'iam sebacamategriease' Per cent N-lauryl sebacamate acid Sodium hydroxide-flake 1 200/100"--F. s. s. Coastal pale oil 89 Salt content 10.6
The N -lauryl sebac amie acid and oil are added to a kettleand heated to about 400-440 F. The sodium hydroxide'is'" dissolved'in three times its weight of water and is slowly added to the heated sebacamic acid and oil in thelkettle. Reaction commences. The addition of the alkali solution is controlled so that the temperature is about 435 F. when all. of the alkali has been completely added; the grease iscooled to about 120 F. maximum without disturbing, that is, without raking, stirring or otherwise agitating it. The grease is then milled that is, passed over rollers, kettle stirred, or passed through-a homogenizer or-milluntil the structure is substantially homog'eneous.
, The above grease, had the following properties:
Penetration ASTM- (American Society for Testing Materials) D-217-47T -296 Droppingpoint .(D./P.) AS'IM,566-42 -1379 l3; Watertolerance Chrysler 10% Color V Straw 48. welamyl-lithium.sebacamate grease The batch was made exactly as in Example 47 The finished grease had the following properties: ,7
Penetration ASTM D-21'7-47T 320 D./P.ASTM D-566-42 409 F.
Water tolerance Chrysler Less tha'n10% 18 49. N-Zauryl-Zithi'am sebacamate grease v Per cent N-lauryl-sebacamic acid 10 Lithium hydroxide 'monohydrate 1 3500/1U0 F. S. S. U. Residual black Oil--- 39 I 100 Salt content ;t; 10.13
The batch was made exactly as in Example 47. The finished grease had the following properties:
Penetration ASTM D-217- C. R. C. wheel bearing grease test Fair to good Rust prevention-10% salt. 7
spray O. K. after 72 hours 50. N-ZauryZ-barium sebacamate grease Per cent N -lauryl-s'ebacai'nic acid 11.44 Barium hydroxide octahydrate 4.28
ZOO/210 F. S. S. U. Mid-Continent semibright stock. 84.28
i 7 j 100.00- Salt content s.. 13.25
The batch was made'exact'lyas in Example 47' except that crystals of alkali were used. The finished grease had the following properties:
Penetration ASTM man-471p, "295 D./P. ASTM D '566 42 ass-F. C. R. C. wheel bearing grease test Good Water tolerance Chrysler Less than 10% 51. N-lauryl-calcium sebacamate grease 11 u I oa o-coHl)to- N o- H25- 2 Per cent N -lauryl-sebacam'ic acid .l 10
Calcium hydroxide-% 200-mesh l 200/210 F. S. S. U. lVfid-Continentsemr bright stock 8-9 Salt content 10.62
The batch was processed as in Example '47, except that the lime was made up as a 1:3 slurry in oil. The finished grease had' the following The batch was processed as in Example 50-. The finished grease had the following properties:
Penetration ASTM D217-47T 311 l3./P. ns'r n-eeegizn uu'. ;1;.1 310 F. 53. N-ZauryZ-Zithium sebacamate grease Per cent N-lauryl sebacamic acid 10 Lithium hydroxide monohydrate V '1 100/ 100 F. S. S. U. solvent extracted Midf Continent pale'oll '89 "100 Salt content 10.13
The batch was. made exactly as in Example 47. The finished grease had the following properties:
Penetration ASTM D.-217-.4='7.T s32 D./P. ASTM D-566-42; 396F. 54. N-oleyZ-lithium sebacamate grease Per cent N-oleyl-sebacamic.acid 10 Lithium hydroxide monohydrate .75 100/100" F. Coastal pale oil 89.25
p I V "100.00 Salt content 10.02
The batch was made as in Example 47. The finished grease had the following properties:
Penetration ASTM D-217-47T 316 D./P. ASTM D-566-42 405 F.
' 55. N-oZegZ-lithium sebacamate grease I Per cent N-oleyl-sebacamic acid 10 Lithium hydroxide monohydrate .75 300/ 100 F. S. S. U. Tech. white oi1 89.2 5
1 I p 100.00 Salt content 10.02
The batch was made as in Example 47. The finished grease had the following properties:
Penetration ASTM D-217-47T 327 D./P. ASTM D-566-42 395 F.
56. N-Zauryl-sodiam sebacamate grease v j V Percent N-lauryl-sebacamic acid Sodium hydroxide 1 1 100/ 100 F. S. S. U. Coastal pale oil 89 Salt content 10.6
The batch was made as Example 47. The finished grease had the following properties: Penetration ASTM D-217-47T "'270 D./P. ASTM D-56642 360 F.
Water tolerance Chrysler 70% 57. N -ZauryZ-Zithium sebaeamate grease v Per cent Noleyl-sebacamic acid 10 Lithium hydroxide monohydrate 1 200/100 F. S. S. U. Mid-Continent pale oil 44.5 180/210 F. S. S. U. Mid-Continent bright. stock 44.5
Salt content 10.13
20 i ez at w m de a in. E a l 4 .r finished rea e had the f l ow pro er es; Penetration ASTM D-217-47T 298 D./P. ASTM D-566-42 427 F. Water tolerance Chrysler 10% 58. N-lauryZ-sodium. sebacamate grease Per cent N-lauryl-sebacamic acid 15.00 Sodium hydroxide -1 1.50
180/210 F. S. S. U. Mid-Continent bright stock 41.75
200/100 F. S. S. U. Mid-Continent pale oil 41.75
. ,7 7 100.00 Salt content V 15.9
The batch Wasmade as. in Exa n'lple, 47." Thefinished grease had the following'properties:
The batch was made as in'ExampleY47. The finished grease had the following-properties:-
Penetration ASTM D-2l7-47T 240- D./P. ASTM D-566-42 F 410 60. N-palmityl-sodium sebacamate grease e 1 Per cent N-palmityl-sebacamic 'acid' 10.0 Sodium hydroxide '1 0.9 3'500/100 F. S. S. U. Residual black 0i1 89.1
Salt content 10.51
The batch was made as in Example l 7. The finished grease had the following properties: Penetration ASTM D-217 l7'-1. L' 245 D./P. ASTM D-566-42 1 F 371 The grease of Example 60.=was" dilutedfurther with Residual black oil 3500/l00 F. S. S. U. at room temperature so that the salt content in the formula was about 2.9%. The properties of this composition were:
300 100 F. s. s. U. Coastal paieen 123.33
if 9 Salt content; 1 6.42
21 The. batch was made as in Example 47. The finished grease had the following properties:
The batch was made as in Example 47. The finished grease had the following properties:
Penetration ASTM D-217-47T 330 D./P. ASTMv D-566-42 F 395 64. N-ZduryZ-Zithium sebacamate grease Percent N-lauryl-sebacamic acid 4.0 Lithium hydroxide monohydrate 0.4 ISO/210 F. S. S. U.'.R'esidua1 black oil 57.3 100/100" F. S. S. U. Coastal pale oil 38.3
Salt content 4.05
The batch was made as in Example 47. The finished grease had the following properties:
Penetration ASTM D-21747T 348 D./P. ASTM D-566-42 F 395 65.. N-stearyl lithium itaconamate grease HH Q CH2: ',G-N?*C10H1 I I Per cent N-stearyl-itaconamic acid 10.0 Lithium hydroxide monohydrate 1. 1 75/210" F. S. S. U. Mid-Continent bright stock 83.9
Salt content 10.23
The batch was made as in Example 47. The finished grease had the following properties:
75/210 F. S. S. U. Mid-Continent bright stock 88.55
Salt content -1 9.46
The batch was made as, in Example 47. The finished grease had theiollowing properties:
Penetration ASTM D-217-47T 326 D./P. ASTM D-566-42' F. 391
. 22 67. N-diZauryl-lzthium adipamate-grease- Lao-0+1elephant-awn 1% a 1 Percent N-dilauryl-adipamic acid -1 10.0 Lithium hydroxide monohydrate 0.87 300/100 F. Mid-Continent pale 011 89.13
p A v 100.00 salt content lQ L;.. a1 10.21
The batch was made as in Example 47. The finished grease had the following properties:
Penetration ASTM'D-217-47T 310 D./P, ASTM D-56'6-42 "9E1. 411 I C. R. .0. wheel bearing grease test Good 63. N -stearyZ-Zithium azeZ-aiimate grease The batch was made as in Example 47. The finished grease had the following properties:
Penetration ASTM D-2'1-7-47T ..1 295 D./P. ASTM 13-566-42 F 416 69. N-butyZ-Zz'thium sebcwamate grease Percent N-butyl-sebacamic acid ....1 10.0 Lithium hydroxide monohydrate 1.63
GOO/ F. Mid-Continent lube distillate .1.. 88.37
Salt content 10.38
The batch was made as in Example 47. The finished greasehad the following properties:
Penetration ASTM D-217-47T 310- D./P. ASTM D-566-42 .F 394' 70. N-oleyZ-Zithium sebacamate grease Per cent N-oleyl sebacamic acid 1.0 Lithium hydroxidemonohydrate 0.09 IOU/100 F. S. S. U. Coastal pale oil 8.9 300/100 F. S. S. U. Coastal pale oil 90.01
100.00 Salt content 71.02
Viscosity (Gardiner Mobilometer at 77 F.) 1 1 100 10oo Po'ur point F -15 This test is made with'a series of disks numbered from 1 to 3 with arbitrary weights, the viscosity being meas- 7 ured by 'disk;movement through the material tested and being represented in seconds.
23 Theabove Gardner Mobilometer viscosity is designated as 1-100-1000 which represents #1 disk, 100 gm. weight, and 1000 seconds at 77 F. Gardner Mobilometer viscosities hereinafter referred to are simply designated similarly to the expression quoted above.
' 71. N-laur yZ-lithium sebccdffiatc grease] in Per cent N-lauryl-sebacamic acid 30 Lithium hydroxide monohydrate A 2.3 300/100 F. Mid-Continent neutral 67.7
7 Y 100.0 Salt content 30.39
The batch was made as in Example 47. .The finished grease had the following properties:
Penetration ASTM D-217-47'I' 107 D./P. ASTM D-566-f12 F 471 Water tolerance Chrysler Nil 72. N-ZduryZ-potdssz'wm sebacamdte grease v Per cent N-lauryl-sebacamic acid 10.0 Potassium hydroxide 1.5 75/210 F. S. S. U. Coastal bright stock 88.5
100.0 Salt content 11.06
Thebatch was made as in Example 47. The finished grease had the following properties:
- Penetration ASTM D-217-47T 342 D./P. ASTM D-566-42 F 379 Water tolerance Chrysler ..per cent" 30 v 73. N-Zauryl-Zithium sebacamate grease Per cent, N-lauryl-sebacamicacid '10 Lithium hydroxide 1 180/210 F. S. S. U. Coastal cylinder stock '87 Lead naphthenate (30% lead) 2 h H v H 100 Salt content 1 10.13
The 180/210 F. S. S. U. Coastal cylinder stock and N-lauryl sebacamic acid were heated to 400 F. with constant agitation. After the acid had completely melted and dispersed in the oil, the neutralization with the lithium hydroxide (15-20%) solution in water was begun. The neutralization was carried out and the grease processed, without leadnaphthenate, as described in Example 47.
After the grease had cooled to room tempera; ture, it was melted to a smooth, homogeneous consistency, after which the lead naphthenate; was added and blended in. It must be noted that the lead naphthenate should not be included in. the high temperature phase operation in this grease formulation.
The physical properties of-the resultant grease were:.-v Penetration-unworked 1 Penetration ASTM D217-47T Penetration-$000, strokes 320 Rustpreventive: test (10% salt spray) a ie c after72jhours N llqury mithium sebacdmate crease v .Percent N-lauryl-sebacamic acid 5.0 Lithium hydroxide monohydrate 0.5
180/210 F. S. S. U. Coastal cylinder stock 92.5 Lead naphthenate (30% lead) 2.0
Salt content 5.06
The batch was made exactly as in Example 73. The physical properties of the resultant grease were:
Penetration-unworked 302 It is to be noted that due "to the sulfur 1.. the,
sulfurized lard oil, that material can not be included in the high temperature operation in the manufacture of these greases, so that the N- lauryl sebacamic acid and the mineral oil are heated to 400 F. and processed as in Example 47.
After the grease had been melted to a homogeneous mass, the sulfurized lard oil was blended into the grease. H V
The resultant grease had the following proper ties:
Viscosity Mobiloineter .at 77 F.) 2-50-(40 to 50) Almen test carries 20 1b. lever.
' arm load Falex test -(5OO lb. st'ept'est) 3000 lbs. gauge Falex test lb. step test) -2700 lbs. gauge Water tolerance Chrysler 10% Y Heat stability test; If?
Since the material is wholly fluid, standard dropping points as a measurement of heat or' temperature resistance could not. be applied. In this case, then, Gardner Mobilometer tests were run at varying temperatures:
At 77 F. actual run 43 seconds 3 I 7 was At 100 F. actual run I was 42 seconds At F. actual run was 42 seconds At actuaL-run was 40seconds. At 200 F. actual run was 40 fsecondsllfi'i 76. N-lauryZ-lithiunt sebacamate grease Per cent N-lauryl sebacamic acid 0.5 Lithium hydroxide monohydrate 0.05 180/210 F. S. S. -U. Coastal cylinder stock 69.60 100/100 F. S. S. U. Coastal palefoil 29.85
' 1 100.00 Salt content 5 The batch was made as in Example 47. The resultant grease had the following properties: Viscosity (Gardner Mobil- 7 ometer at 77 F.) 2-50-(30 to 40) Water tolerance Chrysler 10% Heat stability test (Gardner The heat stability test indicated that the grease does not thin out rapidly as the tempera ture is elevated under ordinary operating conditions. 1
77. Aluminum-mofio-N-lauryl sebacamate grease 392 parts of the sodium salt of the N-lauryl sebacamic acid were dissolved in 1000 parts of water at room temperature. To this solution were added 80 parts of sodium hydroxide. When the above solution was homogeneous, it was heated to boiling, about 212 F. A solution made up of 171 parts of aluminum sulfate nonahydrate dissolved in 500 parts or water was slowly added to the first solution. Boiling was maintained and, after all of thesolution had been added, the boiling was continued for30 minutes. The salt which had risen to the top of the aqueous portion was separated from the aqueous portion by siphoning off the aqueous portion. Fresh water was added to the salt and reboiled. This separation and reboiling was co-ntinuedwith fresh wateruntil the aqueous portion was neutral to phenolphthalein. The salt was then dried and powdered.
A mixture of the aluminum salt and oil to make the grease was prepared in the following manner: 1
' Per cent Aluminum 'mono-N-lauryl sebacamatenui 1O 300/100 F. S. S. U. Coastal pal oil 90 grease was milled out to a homogeneous mass.
The finished grease had the following properties:
Penetration ASTM D-217-47T 346 D./P. ASTM D-56642 F 316 Water tolerance Chrysler -per cent. 25
78. AZuminum-di-N-Zauryl sebacamate grease .iA1( 0%-( CHa)a- --C12 2s)2 OH 1 To 392 parts of sodium N-lauryl sebacamate (prepared as hereinbelow, .Examplefl) dissolved in 1000 parts of Water was added 126 parts of aluminum sulfate nonahydrate dissolved in 500 parts of water. The mass was heated to boiling. The precipitate formed was purified by subsequent washings with boilingdistilled water until washings were neutral to phenolphthalein. The washed precipitate was dried and powdered.
A mixture of the aluminum salt and oil to make the greasewas prepared in the following manner:
Percent Aluminum di-N-lauryl sebacamate; '10
300/ F. S. S. U. Mid continent pale oiL The powdered aluminum di-N-lauryl sebacamate and the oil were mixed in a kettle toa pasty consistency and. were then gradually heatedto about 440 F. with continuous agitation. The mass changes from a pasty opaque mass to a transparent fiuidafter heating for about 20 minutes. The mass was allowed to cool to room temperature without agitation. When cool, the mass was milled out smooth by agitating in'the kettle. The resulting product was a smooth, adhesive, transparent grease. The grease had the following properties:
Penetration ASTM D-217-47T 310 v D./P. ASTM D-566-l2 -394 F. Water tolerance Chrysler 15% Color Golden Yellow C. R.. C. wheel bearing grease test Fair Rust preventive (10% salt spray) O. K. after 72 hours '79. Aluminum tri-N-o'leyl 'adipamate grease 420 parts of sodium N-oleyl' adipamate (pre" pared as hereinloelow, Example 80) were dissolved in 1000 parts of water and the whole was brought to a boil. To the hot salt solution was slowly added the hot solution of 57 parts of aluminum sulfate nonahydrate in 300 parts j of water. Since there were-three (3) parts of sodium salt in excess, the reaction mixture was alkaline to phenolphthalein. The aluminum salt was purified by several washings of boiling water, until the washings were neutral to phenolphthalein. The salt was. then dried and powdered. 1
A mixture of the-aluminum salt and oil to make the grease was prepared inthe following manner:
The finished grease had the following lproperties: i
Penetration ASTM D-2l7-4.7T s30 D./P. ASTM D-366-42 F 344 Water tolerance Chrysler per cent 15 The following procedure was used to make the sodium salts of the amic acids in their separate form. These sodium salts' were used in the preparation of the aluminum salts above.
80. Process for making alkali metal and alkaline earth metal salts of amic acids Na-O- alcohol was added and was found sufiicient to give the phenolphthalein color test. The phenolphthalein color indication was just discharged by introduction of carbon dioxide gas into the solution. Then the alcohol was distilled off, and the anhydrous salt (sodium N -lauryl sebacamate) was pulverized at l F.
A similar process to the above may be employed for producing the other alkali metal salts of the various amic acids. V
The alkaline earth metal salts of the various amic acids may be made in a similar manner to the aluminum'salts made above, namely, by combining the alkali metal salt of the amic acid in water solution with the appropriate alkaline earth chloride or other water-soluble alkaline earth salt. Purification is accomplished in the same manner as stated for the aluminum salts above.
(111) MIXEDAMIC': ACIDS GREASE?) TI-IEREFROM Y a It has been found in accordance with our invention that by using mixtures of one or more difierent salts of amic acids, we may vary the properties thereof and of the greases therefrom advantageously. For example, but without limitation, we may improve the water tolerance characteristic of a grease by using a grease ingredient having an exceptional water tolerance, such as but without limitation, a salt of N-stearyl sebacamic acid; or rust protection may be improved by using a salt of N-oleyl sebacamic acid; or shear stability may be improved by using a salt of N- lauryl sebacamic acid; or dropping point may be improved by using a salt of N-octyl sebacamic acid. These various salts of amic acids mentioned in this paragraph may be combined with one another or with other herein mentioned amic acid salts to give the properties desired.
We have found that there are available commerically certain amines which contain varying proportions of primary and secondary amines.
Illustrative of the mixed amines, but without limitation, is a technical lauryl amine of the-following constituency:
Per cent Primary amines 85 Octyl amine per cent" 8 v Decyl amine"; do 9 Dodecyl (lauryl) amine do 47 Tetradecylamine do 18 Hexadecylamine do 8 Octadecylamine do Octadecenylamine do 5 Mixed secondary amines This mixed amine will produce, of course. a
mixture of the corresponding amic acids with the dibasic acid selected.
By test, it wasdetermined that the reacting (equivalent) weight of the technical laurylamine is 235. This weight was then used in determining the reaction mixtures of the acid and amine in the preparation of amic acids as follows:
81. N-Tech. Zauryl-adipamic acid and other like compounds of different hydrocarbon chain lengths in the. amine group.
Parts Tech. laurylamine m l 235 (61.7%) Adipic acid 146 (33.3%)
The amic acid was made in the same way as provided in Example 4. V e
The amic acid had the following properties:
Test Data Theoretical Actual 7 I I Parts Tech. laurylamine -i 235 (53.6%) Sebacic acid i 203 46.4%)
The amic acid was made in the same way as provided in Example 4. V
The amic acid had the following properties:
Test Data Theoretical Actual Yield "percent" 95. 8 95. 6 g do 4.? 4. 4
Acidity-calculated as ole 67. 2 67. 4 Mean molecular Weight" 420 418 Melting point 109 C.
1 Iiight tan amorphoussolid.
and'iother like compounds of 'diflerenthydrocaribon chain lengths in the amine group.
. m. xlwipPer cent N-Tech. lauryl sebacamic acid 10 Lithium hydroxide monohydrate l 600/100 F. S. S. U. Coastal cylinder oil blend 89,
The batch was made-exactly asin" Example 47.
The finished grease had the following properties:
Penetration ASTM D-217-47T 276 Penetrationunworked 276 Penetratin5000 strokes 324 D./P. AS'IM D-566-42 416 F. Chrysler basket D./P 367 F. Water tolerance Chrysler 15% C. R. C. wheel bearing grease test O. K.
Rust preventive (10% salt spray) .0. K. after '72 hours G. E;ball bearing test (212 F. at
3450 R. P. M.) 1 O.K. after M 200 hours, no sign of failure The properties represent a combination of properties resulting from the .use of the mixture of amines in the formation of the grease base, which accordingly is a mixture of salts oi the various amic acids made from such amines.
Lubricating greases made with compounds in accordance with our invention are superior to the greases made with the natural fatty materials in that the dropping, points of the greases made in "accordance with our invention are from 50.--75 F. higher than the best natural fat greases of. equivalent gelator content. Also, the amic acid compound greases, because of the polarity of the gelator are rust preventivesand will actually displace water from metal surfaces. and will resist water after the surface has once been treated with the lubricant. In addition, natural fatty materials are mixtures of substances, some of which do not form greases. These non-grease forming substances are present in varying amounts and accordingly change the, greases. In the greases of our invention all ingredients employed. form greases and there is substantially no non-grease forming material.
When properly compounded, our amic acid compound greases can be used at operating ternperatures much nearer their ASTM dropping points than can the natural fat'greases ofequivalent gelator content.
The resistance to shear of our amic. acid greases is much greater than the natural -fat greases of equivalentgelatorcontent.
. The control of the manufacture of the greases of our invention is easier than in the manufacture of natural fat greases. H i
' What we claim is:
1. As a new composition, a mixture containing a substantial proportion of a gelation agent and a petroleum lubricant, said gelation agent being selected from the group consisting of the alkali metal salt of an amic acid having the formula and a polyvalent metal salt of said amic acid, where R is selected from the group consisting of methylene groups having a carbon chain length of 1 to 8 carbon atoms and the group R1 is an aliphatic-radical of a carbon chain length of 4 to 18 carbon atoms,'and R2 is selected from the group consisting of hydrogen and an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms.
2. As a new-composition, a mixture containing I a substantial proportion of a gelation age'nt'and a petroleum lubricant,- said gelation agent'being R1 is an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms,and-R,z is selected from the group consisting of hydrogen and an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms.
3. As a new composition, a mixture containing a substantial proportionof a gelation agent and a petroleum lubricant, said gelation agent being a compound having the formula v 0 Ill 0 where M is an alkaline earth metal R. is selected from the group consisting of methylene groups having a carbon chain'of -1 to 8. carbon atoms and the group .i
R2 is an aliphatic radical. of a carbon chain length of 4 to 18 carbon atomsgand R3 is selectedfrom the group consisting of hydrogen. and an amic acid radical having the formula O O i 4. As a new composition, a'mlxture containing a substantial proportion of a gelation" agent and a petroleum lubricant, said gelation agent being a compound having the formula where R iss elected from the group consisting of methylene groups having a carbon chain of 1 to 8 carbon atoms andthe group I I R1 is an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms; R: is selected from the group consisting of hydrogen and an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms. and R3 and R4 are each selected from the group consisting of hydrogen and an amic acid radical having the formula 5. A grease having about 0.5% to 30% grease base of the total weight of the grease, said grease base being selected from the group consisting of an alkali metal salt and a polyvalent metal salt of an amic acid having theformula where R is selected from the group consisting of methylene groups having a carbon chain length of 1 to 8 carbon'atoms and the-group.
R1 is an aliphatic radical of a carbon chain length the group consisting of an'alkali metal salt and a polyvalent metal salt of an amic acid having the formula g t a i HOCR-CN-Rz v where R is selected from the group consisting of methylene groups having a carbon chain length of 1 to 8 carbon atoms and the group i R1 is an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms, and R2 is selected from the group consisting of hydrogen and an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms, and the remainder of the grease being composed principally of petroleum oil.
7. A grease composed of about 0.5 to 30% of N-lauryl.alkali metal sebacamate and the remainder being composed substantially of mineral oil.
8. A grease composed of about to 13% of N-laurylalkaline earth. metal sebacamate and the remainder being composed substantially of mineral oil.
9. A grease composed of about 1 to 10% of N- oleylalkali metal sebacamate and the remainder being composed substantially of mineral oil.
10. A grease "composed of; about 10% of N- =palmityl.alkali' metal sebacamate and the remainder being composed substantially of mineral oil.
11. A grease composed of about 6% of N- laurylalkali metal azelaamate, and the remainder being composed substantially of mineral oil.
12. A grease composed of about 10% of aluminum di-N-lauryl sebacamate and the remainder being composed substantially of mineral oill 13. A composition containing a substantial pro- 0 II o R1 is an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms, and R is selected from the group consisting of hydrogen and an aliphatic radical of a carbon chain length of 4 to 18 carbon atoms.
14. A composition containing a substantial proportion of a gelation agent and a petroleum lubricant, said gelation agent being a mixture of at least two substances selected from the group consisting of an amic acid salt having the formula x-oi-R-t-1L' Rz where X is an alkali metal, R is selected from the group consistin of methylene groups having a carbon chain length 011 to 8 carbon atoms and the group 7 v REFERENCES CITED.
The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,191,738 Balle Feb. 27, 1940 2,191,978 Balle et al Feb. 27, 1940 2,283,602 Fiero May 19, 1942 2,322,783 Katzman et a1. June 29, 1943 2,324,712 Lynch July 20, 1943 2,363,510 Farrington et al. Nov. 28, 1944 2,378,442 Smith et a1 June 19, 1945 2,378,443 Smith et a1 June 19, 1945 2,432,049 Swan et al Dec. 2, 1947 2,458,425 Rocchini Jan. 4, 1949 2,480,743 Krantzet a1. Aug. 30, 1949

Claims (1)

1. AS A NEW COMPOSITION, A MIXTURE CONTAINING A SUBSTANTIAL PROPORTION OF A GELATION AGENT AND A PETROLEUM LUBRICANT, SAID GELATION AGENT BEING SELECTED FROM THE GROUP CONSISTING OF THE ALKALI METAL SALT OF AN AMIC ACID HAVING THE FORMULA
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Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2710839A (en) * 1952-11-01 1955-06-14 Standard Oil Co Aryl-urea thickened greases
US2752312A (en) * 1952-08-19 1956-06-26 California Research Corp Polyamide-polyamate-thickened grease
US2756213A (en) * 1952-08-19 1956-07-24 California Research Corp Amate-dicarboxylate-thickened grease
US2801969A (en) * 1953-02-02 1957-08-06 Exxon Research Engineering Co Lubricating greases thickened with soaps obtained by alkali fusion of amino alcohols
US2820012A (en) * 1954-12-14 1958-01-14 California Research Corp High temperature phthalamate grease compositions
US2830954A (en) * 1955-11-23 1958-04-15 California Research Corp Polyamide grease composition
US2830955A (en) * 1955-11-23 1958-04-15 California Research Corp Polyamide-thickened grease
US2849400A (en) * 1953-12-31 1958-08-26 California Research Corp Greases thickened with polyamido acid salts
US2849401A (en) * 1953-12-31 1958-08-26 California Research Corp Diamido acid salt grease thickeners
US2852466A (en) * 1956-05-24 1958-09-16 California Research Corp Grease compositions wherein the thickener comprises a metal salt of an nu-acylaminoorganocarboxylic acid
US3031282A (en) * 1958-01-07 1962-04-24 Socony Mobil Oil Co Inc Stabilized distillate fuel oil
US3173945A (en) * 1958-10-06 1965-03-16 Socony Mobil Oil Co Inc Itaconamic acids
US3180830A (en) * 1963-07-19 1965-04-27 Texaco Inc Metal working lubricant compositions
US3264075A (en) * 1962-07-06 1966-08-02 Mobil Oil Corp Metal salts of succinamic acids in distillate fuel oil
US3365477A (en) * 1962-07-06 1968-01-23 Mobil Oil Corp Alkoxy metal salts of succinamic acids
US3427245A (en) * 1966-08-15 1969-02-11 Chevron Res Lubricant additive composed of a mixture of amine salts of monoamides and monoamides of alkenyl succinic acids
US3950392A (en) * 1968-12-19 1976-04-13 Alelio Gaetano F D Unsaturated ester-amides of halogenated alkenes
US4675422A (en) * 1985-10-23 1987-06-23 Stepan Company Organometallic compounds
US5166407A (en) * 1992-01-27 1992-11-24 Monsanto Company Process for preparing fatty peroxyacid precursors having amide moieties in the fatty chain
US5206432A (en) * 1992-07-28 1993-04-27 Monsanto Company Process for preparing monoamido acids
US5281746A (en) * 1993-02-01 1994-01-25 Monsanto Company Process for preparing peroxyacid precursors having amide moieties in the fatty chain
WO2010063617A1 (en) * 2008-12-04 2010-06-10 Basf Se Mixtures of itaconic acid or itaconic acid derivatives and primary amines for producing 1,3- and 1,4-alkyl methyl pyrrolidones
WO2013012987A1 (en) * 2011-07-21 2013-01-24 The Lubrizol Corporation Overbased friction modifiers and methods of use thereof

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2180743A (en) * 1939-03-21 1939-11-21 Charles A Martin Machine for cutting tile and the like
US2191738A (en) * 1934-09-01 1940-02-27 Ig Farbenindustrie Ag High-molecular polycarboxylic acid amides and their production
US2191978A (en) * 1935-10-10 1940-02-27 Ig Farbenindustrie Ag Quaternary nitrogen compounds and process of preparing them
US2283602A (en) * 1940-01-09 1942-05-19 George W Fiero Grease and lubricant
US2322783A (en) * 1941-08-23 1943-06-29 Emulsol Corp Preparation of amides
US2324712A (en) * 1940-09-25 1943-07-20 American Cyanamid Co Dialkyl esters of n-substituted aspartic acid and method of preparing the same
US2363510A (en) * 1942-09-15 1944-11-28 Standard Oil Co California Compounded oil
US2378442A (en) * 1944-01-04 1945-06-19 Gulf Oil Corp Mineral oil composition
US2378443A (en) * 1944-12-02 1945-06-19 Gulf Oil Corp Mineral oil composition
US2432049A (en) * 1945-08-31 1947-12-02 Kenneth C Swan Cholinelike compounds
US2458425A (en) * 1947-06-19 1949-01-04 Gulf Research Development Co Oil compositions

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2191738A (en) * 1934-09-01 1940-02-27 Ig Farbenindustrie Ag High-molecular polycarboxylic acid amides and their production
US2191978A (en) * 1935-10-10 1940-02-27 Ig Farbenindustrie Ag Quaternary nitrogen compounds and process of preparing them
US2180743A (en) * 1939-03-21 1939-11-21 Charles A Martin Machine for cutting tile and the like
US2283602A (en) * 1940-01-09 1942-05-19 George W Fiero Grease and lubricant
US2324712A (en) * 1940-09-25 1943-07-20 American Cyanamid Co Dialkyl esters of n-substituted aspartic acid and method of preparing the same
US2322783A (en) * 1941-08-23 1943-06-29 Emulsol Corp Preparation of amides
US2363510A (en) * 1942-09-15 1944-11-28 Standard Oil Co California Compounded oil
US2378442A (en) * 1944-01-04 1945-06-19 Gulf Oil Corp Mineral oil composition
US2378443A (en) * 1944-12-02 1945-06-19 Gulf Oil Corp Mineral oil composition
US2432049A (en) * 1945-08-31 1947-12-02 Kenneth C Swan Cholinelike compounds
US2458425A (en) * 1947-06-19 1949-01-04 Gulf Research Development Co Oil compositions

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2752312A (en) * 1952-08-19 1956-06-26 California Research Corp Polyamide-polyamate-thickened grease
US2756213A (en) * 1952-08-19 1956-07-24 California Research Corp Amate-dicarboxylate-thickened grease
US2710839A (en) * 1952-11-01 1955-06-14 Standard Oil Co Aryl-urea thickened greases
US2801969A (en) * 1953-02-02 1957-08-06 Exxon Research Engineering Co Lubricating greases thickened with soaps obtained by alkali fusion of amino alcohols
US2849400A (en) * 1953-12-31 1958-08-26 California Research Corp Greases thickened with polyamido acid salts
US2849401A (en) * 1953-12-31 1958-08-26 California Research Corp Diamido acid salt grease thickeners
US2820012A (en) * 1954-12-14 1958-01-14 California Research Corp High temperature phthalamate grease compositions
US2830955A (en) * 1955-11-23 1958-04-15 California Research Corp Polyamide-thickened grease
US2830954A (en) * 1955-11-23 1958-04-15 California Research Corp Polyamide grease composition
US2852466A (en) * 1956-05-24 1958-09-16 California Research Corp Grease compositions wherein the thickener comprises a metal salt of an nu-acylaminoorganocarboxylic acid
US3031282A (en) * 1958-01-07 1962-04-24 Socony Mobil Oil Co Inc Stabilized distillate fuel oil
US3173945A (en) * 1958-10-06 1965-03-16 Socony Mobil Oil Co Inc Itaconamic acids
US3365477A (en) * 1962-07-06 1968-01-23 Mobil Oil Corp Alkoxy metal salts of succinamic acids
US3264075A (en) * 1962-07-06 1966-08-02 Mobil Oil Corp Metal salts of succinamic acids in distillate fuel oil
US3180830A (en) * 1963-07-19 1965-04-27 Texaco Inc Metal working lubricant compositions
US3427245A (en) * 1966-08-15 1969-02-11 Chevron Res Lubricant additive composed of a mixture of amine salts of monoamides and monoamides of alkenyl succinic acids
US3950392A (en) * 1968-12-19 1976-04-13 Alelio Gaetano F D Unsaturated ester-amides of halogenated alkenes
US4675422A (en) * 1985-10-23 1987-06-23 Stepan Company Organometallic compounds
US5166407A (en) * 1992-01-27 1992-11-24 Monsanto Company Process for preparing fatty peroxyacid precursors having amide moieties in the fatty chain
US5206432A (en) * 1992-07-28 1993-04-27 Monsanto Company Process for preparing monoamido acids
EP0582560A1 (en) * 1992-07-28 1994-02-09 Akzo Nobel N.V. Process for preparing monoamido acids
US5281746A (en) * 1993-02-01 1994-01-25 Monsanto Company Process for preparing peroxyacid precursors having amide moieties in the fatty chain
WO2010063617A1 (en) * 2008-12-04 2010-06-10 Basf Se Mixtures of itaconic acid or itaconic acid derivatives and primary amines for producing 1,3- and 1,4-alkyl methyl pyrrolidones
US8796472B2 (en) 2008-12-04 2014-08-05 Basf Se Mixtures of itaconic acid or itaconic acid derivatives and primary amines for producing 1,3- and 1,4-alkyl methyl pyrrolidones
WO2013012987A1 (en) * 2011-07-21 2013-01-24 The Lubrizol Corporation Overbased friction modifiers and methods of use thereof
CN103814011A (en) * 2011-07-21 2014-05-21 卢布里佐尔公司 Overbased friction modifiers and methods of use thereof
US9512379B2 (en) 2011-07-21 2016-12-06 The Lubrizol Corporation Overbased friction modifiers and methods of use thereof

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