DE2042279A1 - Method of lubricating aluminum and aluminum alloys - Google Patents
Method of lubricating aluminum and aluminum alloysInfo
- Publication number
- DE2042279A1 DE2042279A1 DE19702042279 DE2042279A DE2042279A1 DE 2042279 A1 DE2042279 A1 DE 2042279A1 DE 19702042279 DE19702042279 DE 19702042279 DE 2042279 A DE2042279 A DE 2042279A DE 2042279 A1 DE2042279 A1 DE 2042279A1
- Authority
- DE
- Germany
- Prior art keywords
- diol
- carbon atoms
- aluminum
- hydrocarbon
- aliphatic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M173/00—Lubricating compositions containing more than 10% water
- C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
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- C10M173/00—Lubricating compositions containing more than 10% water
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/247—Stainless steel
-
- 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
- C10N2050/01—Emulsions, colloids, or micelles
-
- 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
- C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
- C10N2060/04—Oxidation, e.g. ozonisation
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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)
- Shaping Metal By Deep-Drawing, Or The Like (AREA)
Description
j:;. Dirt ...r:.V.. H.-J. WOLFP
'1Ji1V. ii^:-Z CKH. L". E !Lj:;. Dirt ... r: .V .. H.-J. WOLFP
' 1 Ji 1 V. ii ^: - Z CKH. L ". E! L
R A H K J-' L-,- Ϊ A M MAl N - HOCHST RA H K J- 'L -, - Ϊ AM MAl N - H OCHST
Lasers ΙΓγ. 16 481Laser ΙΓγ. 16 481
Chevron Research Company San Francisco, CaI., V.St.A.Chevron Research Company San Francisco, CaI., V.St.A.
Verfahren zum Schmieren von Aluminium und Aluminiumlegierungen Method of lubricating aluminum and aluminum alloys
Die Erfindung betrifft die Verwendung von Diolen beim Schmieren der Oberfläche von Aluminium oder Aluminiumlegierungen während des Zaltverformens, der maschinellen Bearbeitung, Gewindeschneiden und Bohren eingeschlossen, oder in mechanischen Vorrichtungen.The invention relates to the use of diols in lubricating the surface of aluminum or aluminum alloys during forming, machining, Tapping and drilling included, or in mechanical devices.
Beim Walzen von Aluminium oder Aluminiumlegierungen unter Bildung von Blechen oder Folien werden Schmiermittel verwendet, um die Reibung zwischen dem Metall und den Walzen zu verringern und ein gutes Oberflächen-Finish zu erzielen. Die Schmiermittel dienen auch als Wärmeübertragungsmittel, um die in den Walzen und im Metall während des Walzens erzeugte Wärme abzuleiten.When rolling aluminum or aluminum alloys under Forming sheets or foils, lubricants are used to reduce the friction between the metal and the rollers and to achieve a good surface finish. The lubricants also serve as a heat transfer medium, to dissipate the heat generated in the rolls and in the metal during rolling.
Die beim Walzen von Aluminium verwendeten Schmiermittel stellen fast immer Mischungen aus polaren oder "öligen" Zusätzen und einem leichten Mineralöl, einem synthetischen Kohlenwasserstofföl, einem Petroleumdestillat oder WasserThe lubricants used in rolling aluminum are almost always mixtures of polar or "oily" Additives and a light mineral oil, a synthetic one Hydrocarbon oil, a petroleum distillate or water
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dar. Die Zusätze in den -jalzschmiermitteln sollen oie Schmierfähigkeit des Ols oder wassers verbessern, um so die Reibung beim Eingriff zwischen 7/alze und Metall zu verringern, üine Verringerung der Reibung ermöglicht eine Verringerung der Dicke des auszuwalzenden Metalls. Die Zusätze dienen auf Grund ihrer chemischen oder polaren Wirkung auch zur Verringerung der neigung des Metalls, während des 'walzens auf der Oberfläche der V/alze anzuhaften.The additives in the rolling lubricants should oie lubricity improve the oil or water in order to reduce the friction when engaging between 7 / alze and metal, A reduction in friction enables a reduction the thickness of the metal to be rolled. The additives are also used because of their chemical or polar effect Reduction of the tendency of the metal to adhere to the surface of the roller during rolling.
Ähnliche Schmiermittel werden zum Schmieren von Aluminiumteilen in Με schinen, Getrieben und anderen Vorrichtungen verwendet. Hier sind die Probleme besonders akut,und das Fehlen eines geeigneten Aluminiumschmiermittels hat die Entwicklung von Maschinen mit nicht-ausgekleideten Aluminiumzylindern stark beschränkt.Similar lubricants are used to lubricate aluminum parts used in Με machines, gears and other devices. Here the problems are particularly acute, and that The lack of a suitable aluminum lubricant has led to the development of machines with non-lined aluminum cylinders severely limited.
Die maschinelle Bearbeitung von Aluminium erfordert ebenfalls Schmiermittel. Das Fehlen geeigneter Schmiermittel beim Bohren, Gewindeschneiden oder anderen maschinellen Bearbeitungsprozessen von Aluminium verkürzt die brauchbare Lebensdauer von Werkzeugen, wie Bohrern und Gewindeschneidvorrichtungen wesentlich.Machining aluminum also requires lubricants. The lack of suitable lubricants when drilling, tapping or other machining processes of aluminum shortens the useful Life of tools such as drills and thread cutting devices essential.
In den USA-Patentschriften 2 193 631 und 2 350 570 sind langkettige einwertige Alkohole als Komponenten von Schmiermitteln beschrieben. Nach der USA-Patentschrift 2 962 401 wird ein einen gesättigten aliphatischen Alkohol mit weniger als acht Kohlenstoffatomen enthaltendes Aluminiumschmiermittel verwendet. Die USA-Patentschrift 3 124 531 erläutert ein Polypropylenglykol enthaltendes Aluminiumschmiermittel. Von Guminski et al. ist in J. of the Inst, of Metals, Bd. 88, S. 481 (1959-1960) die Verwendung von 1,10 Decandiol in einem Aluminiumschmiermittel auf der Basis n-Propanol beschrieben. Long-chain monohydric alcohols are described as components of lubricants in U.S. Patents 2,193,631 and 2,350,570. According to U.S. Patent 2,962,401, an aluminum lubricant containing a saturated aliphatic alcohol having fewer than eight carbon atoms is used. U.S. Patent 3,124,531 discloses an aluminum lubricant containing polypropylene glycol. From Guminski et al. the use of 1.10 decanediol in an aluminum lubricant based on n-propanol is described in J. of the Inst, of Metals, Vol. 88, p. 481 (1959-1960).
109810/2 01 S . BAD ORIGINAL109810/2 01 p. BATH ORIGINAL
2U422792U42279
Beim erfindungsgenä-'iien Verfahren sun! Sermieren von Aluminium und ^liuuiniumle.-ierungen während des Kaltverformens, o.er maschinellen Bearbeitung oder anderen mechanischen Prozessen wird auf die Oberfläche des Aluminiums oder der Aluminiumlegierung ein Schmiermittel aufgebracht, das einen größeren Teil einer 'Irafeerflussi^keit und einen kleineren feil eines Ο.,-ΰ-τ-, Diols enthält, bei de:i: die beiden Hydroxylgruppen an cenachb^rte odec durch ein Kohlenstoffatom getrennte ivar.lenstoffatome gebunden i=inö. Die Trä^erflüssiirkeit k-Λ'Λΐι ein i-.iner?lölr ein synthetisches Aöhlenwrasser&tofföl," ein PeTroieu:;ic.estillat, ein haioceuierter oder oxygenierter xvoiilemvasseretoff oder ".."asser sein.In the inventive method sun! Serming of aluminum and ^ liuuiniumle.-ionen during cold working, machining or other mechanical processes, a lubricant is applied to the surface of the aluminum or the aluminum alloy, which contains a larger part of a 'Irafeerflussi ^ keit and a smaller part of a Ο ., - ΰ-τ-, diol contains, in de: i: the two hydroxyl groups bonded to cenachb ^ rte odec by a carbon atom separated ivar.lenstoffatome i = inö. The Trä ^ erflüssiirkeit k Λ'Λΐι an i-.iner löl r a synthetic Aöhlenw r ater & tofföl? "One PeTroieu:; ic.estillat, a haioceuierter or oxygenated xvoiilemvasseretoff or" be .. "ater.
3ei den erfineun.i'sgemäß vervrendeten Diolen handelt es eich um C-iq-Cv- Diole mit den folgenden gesättigten oder &roi;.atisch ungesätti-rten . Struktur einheit entIn the case of the diols used in accordance with the invention, it is a matter of course around C-iq-Cv diols with the following saturated or .atic unsaturated. Structure unit ent
OH OEOH OE
1 " ' ■ t ι 1 "'■ t ι
ii) — σ — σ — σ-Ι I Iii) - σ - σ - σ-Ι I I
CK OH
III) 'C =as σ-
oderCK OH
III) 'C = as σ- or
IV)IV)
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2U422792U42279
Die allgeiütine Formel des 'JDiols istThe general formula of 'JDiol is
V) (R1)V) (R 1 )
(H6)(H 6 )
in α erin α er
1; öie kleinen duchstcben a, Td und d bis h G oder 1 bedeuten U2id Mindestens 2 BucJbstcben 1 sind;1; The small letters a, Td and d to h mean G or 1 U2id At least 2 columns are 1;
1 61 6
>) R und R bedeuten wasserstoff oder eine Kohlenv/asserstoff.;:ru;.pe mit 1 bis 28 Kohlenstoffatomen und>) R and R mean hydrogen or a carbon. : ru; .pe with 1 to 28 carbon atoms and
3) K , R/, R und i\ sind Loijienv/asserstofi'^ruppen mit 1 eis 12, vorzu::_GV/eise 1 bis 6 Kohlenstoff atomen, und V/ei3) K, R / R and i \ are Loijienv / asserstofi '^' groups having 1 ice 12, vorzu: / else 1 to 6 carbon atoms _GV, and V / ei
>4> 4
i. und R oder K und R zusanrnen einen carbocyclischen Kin% oilcen,- hrb^n sie gemeinsam 2 bis 28 und vorzugsweise 4 bis 2o kohlenstoff ε tome. jjie G-esamtcnsphl r3er xiir.^KOhlenstof fs tome beträgt 4 bis fc, vorzugsweise 5 bis 7 und insbesondere 6.i. and R or K and R combine to form a carbocyclic kin% - they together have 2 to 28 and preferably 4 to 20 carbon atoms. jjie G-esamtcnsphl r 3 XIIR. ^ CARBON fs tome is 4 to fc, preferably 5 to 7 and in particular 6.
.bei d ,n α-Liolen.at d, n α-Liolen
f = 0; bei den .ΐ-jjiolen ist f = 1.f = 0; in the case of the .ΐ-jjiols, f = 1.
liie ivoi'iiensto J'atorne können in Form von geradkettig en oder versv/eif ten sliphc tischen, cyclo^liphr: tischen, Aryl- oder f:liphstisch cubstitui^rten jirylkonfi '_.urationen vorli· i on. -.enn f = C und b ur.d g beide 1 und e und/oder h = v. i;;t, kernen R^ und R^ ;:u::·· .amen mit ο en Ivchliriistoff f tomen, ijn (.it sit ^g. cunden rind, einen corhccyc] ischen (d.h. einen alicyclischen oder f-romati^ciien) oder einen suDi-tituierten curbocyclisc;ien η in * bil(ien. iüinlie1· können, v.'ei.n a, e und f jeweils 1 und b und d jev.'eils ü sind, R und R :-:uHiimiiien i.'-it den i\oh c-nstoffatomen, ·?η die si.e gebunden sind, einen c i'bocyclischen oder substituierten car'bocyclisohen j\ing blinen.liie ivoi'iiensto J'atorne can en straight in the form of or versv / cif th sliphc-Nazi, cyclo ^ liphr: schematically, aryl or f: liphstisch cubstitui ^ rten jirylkonfi '_.urationen vorli · i on. -.enn f = C and b and dg both 1 and e and / or h = v. i ;; t, kernels R ^ and R ^;: u :: ·· .amen with ο en Ivchliriistoff f tomen, i j n (.it sit ^ g. cunden beef, a corhccyc] ischen (i.e. an alicyclic or f -romati ^ ciien) or a suDi-tituated curbocyclisc ; ien η in * bil (ien. iüinlie 1 · can, v.'ei.na, e and f respectively 1 and b and d jev.'eils ü are, R and R: -: uHiimiiien i .'- it the i \ oh c -nstoffatomen, ·? Η which are bound, a c i'bocyclischen or substituted car'bocyclishen j \ ing blink.
1 Π 9 B 1 Q / 2 0 1 b1 Π 9 B 1 Q / 2 0 1 b
BADBATH
_ 5 —_ 5 -
Bevorzugte Strukturen umfassenPreferred structures include
OH OHOH OH
1 I '1 I '
VI) R1 OH. — CH-RVI) R 1 OH. - CH-R
OHOH
YII) R1 OH— CHj- CH — R6 YII) R 1 OH - CHj - CH - R 6
YIIl)YIIl)
undand
IX)IX)
1) R , R und R die oben angegebene Bedeutung haben und1) R, R and R have the meaning given above and
2) R7, R8, R9 und R10 [jeweils Wasserstoff oder einen Kohlenwasserstoff rest mit 1 bis 24, vorzugsweise 4 bis 20 Kohlenstoffatomen bedeuten.2) R 7 , R 8 , R 9 and R 10 [each denote hydrogen or a hydrocarbon radical having 1 to 24, preferably 4 to 20 carbon atoms.
Die Struktur YI kann als aliphatisch.es a-Diol,- die Struktur YII als aliphatisches ß-Diol, die Struktur VIII alsThe structure YI can be used as aliphatic.es a-diol, - the structure YII as an aliphatic ß-diol, the structure VIII as
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2 ί; 42 27 92 ί; 42 27 9
Catechin und die ütruk'.;ur IX als gemischtes bezeichnet v/erden.Catechin and the ütruk '.; Ur IX as mixed denotes v / earth.
.3eim Scnmieren von Aluminium ist es wichtig, daß Materialien, cie sich nachteilig auf die Aluminiumoberflache auswirken, nicht im Schmiermittel enthalten sind. Dementsprechend weisen die Diole. gemäß der Erfindung keine anderen Atome als Kohlenstoff-, Wasserstoff- und Sauerstoffatome auf. Ebenso sollte die Trägerflüssigkeit keine anderen Atome als Kohlenstoff-, Wasserstoff-, Sauerstoff- und Halogenatome enthalten..3When lubricating aluminum, it is important that materials cie adversely affect the aluminum surface, are not contained in the lubricant. The diols show accordingly. according to the invention no others Atoms as carbon, hydrogen and oxygen atoms on. Likewise, the carrier liquid should not contain any atoms other than carbon, hydrogen, oxygen and halogen atoms contain.
Für die erf indungsgemäI3en Zwecke brauchbare Mole sind cc-Diole (f = 0) und ß-Diole (f = 1), wie 1,2- und 1,3-C10-C50 Alkandiole und C-|o~C3O Dihydroxyalkylbenzole. Spezielle Beispiele sind 1,2-n-Decandiol, 1,3-n-Decandiol, 1,2-n-Dodecandiol, 1,3-n-Dodecandiol, 1,2-n-Hexadecandiol, 1,3-n-Hexadecandiol, 1,2-n-Eicosanäiol, 1,3-n-Eicosandiol, 4,5-n-Hexadecandiol, 4,6-n-Kexadecandiol, 1,2-Dihydroxybenzol, 1,2-Dihydroxynaphthalin, 1,2-Dihydroxy-3-n-hexy!benzol, 1 ,3-Dihydroxy-5~:n-decyrbenzol, 4-A'thyl-4-(31 ,4' -dihydroxy)-pheny!heptan, 1,4-Dihexyl-2,3~dihydroxybenzol, 2-(1'-Hydroxyäthyl)-4-(1",3",5",7"-tetramethyloctyl)phenol, 2-(1'-Hydroxypropyl)-4-(1",1"-dipropylbutyl)phenol und 6,8,10,12-Tetrame thyldecan-1 ,2-diol.Moles which can be used for the purposes according to the invention are cc-diols (f = 0) and β-diols (f = 1), such as 1,2- and 1,3-C 10 -C 50 alkanediols and C- | o ~ C 3O Dihydroxyalkylbenzenes. Specific examples are 1,2-n-decanediol, 1,3-n-decanediol, 1,2-n-dodecanediol, 1,3-n-dodecanediol, 1,2-n-hexadecanediol, 1,3-n-hexadecanediol 1,2-n-eicosanediol, 1,3-n-eicosanediol, 4,5-n-hexadecanediol, 4,6-n-kexadecanediol, 1,2-dihydroxybenzene, 1,2-dihydroxynaphthalene, 1,2-dihydroxy -3-n-hexy! Benzene, 1,3-dihydroxy-5 ~: n-decyrbenzene, 4-ethyl-4- (3 1 , 4 '-dihydroxy) -pheny! Heptane, 1,4-dihexyl- 2,3 ~ dihydroxybenzene, 2- (1'-hydroxyethyl) -4- (1 ", 3", 5 ", 7" -tetramethyloctyl) phenol, 2- (1'-hydroxypropyl) -4- (1 ", 1 "-dipropylbutyl) phenol and 6,8,10,12-tetramethyldecane-1,2-diol.
Eine besonders bevorzugte Gruppe von Diolen sind endständige aliphatisch^ Diole der FormelA particularly preferred group of diols are terminal aliphatic ^ diols of the formula
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2 ü 4 2 2 7 92 ü 4 2 2 7 9
OB ίOB ί
-Ο —-Ο -
(κ2).(κ 2 ).
Οίι.ΟΗΟίι.ΟΗ
-I ! ■ --I! ■ -
in aer R eine aliphatiache kohlenwasserstoff gruppe r.:It 7 bis 26 kohlenstoffatomen darstellt und cie anderen o: lnbole die oben angegebene Jedeut-uni haben. Repräsentativein aer R an aliphatic hydrocarbon group r.:It Represents 7 to 26 carbon atoms and the other o: lboles have the Jedeut-uni given above. Representative
~ 2 "*■~ 2 "* ■
Beispiele für diese Diole sind solche, in deren R ,Ϊ/ undExamples of these diols are those in whose R , Ϊ / and
R^ sämtlich './ascerstoff bedeuten U2id a = 1 iet. bie -a":~h eile allgemeine formelR ^ all './ascstoff mean U2id a = 1 iet. bie -a ": ~ h hurry general formula
λ!)λ!)
R1IR 1 I
- ί- ί
Ch ,0HCh, OH
-is ist ■ -ichtig, äaiB sich nicht" mehr :1s ein-Kohlenstoffetom zwischen äeii kohlenstoffatomen in der Kei;te befindet, r-n. welche die beiden Hydroxygruppen -;-bunaen cind, d.h. in der obigen i'oriiiel V ist f = O oder 1. In den 3-Di öl en sir.d äementscrecliend cie Hydroxygruppen r:n v;eixesten voneinsnder entfernt. 2s '.."uröe gefunden, är.I Uiole, in denen die Hy5rox; en veiter v^nein?-näor entfernt sind, äie überlegenen treigjnsohaften. der erfincr.n .st:einä.i;en Liole nicht besitzen. Vieiraehr haben Diole mit v.T-?i";er voneinander, entfernten hydroxygruop'en die Li^en&chef ten einv.rerti; er jiikonole. die, wie nachstehend 6ec-eigt v;ird. den erfindun^sgeitE-iei: α- und ß-Dioleii v:eit unt;:rlet:eii cind.-is is correct, if there is no longer a one-carbon atom between the carbon atoms in the kernel, rn. which the two hydroxyl groups -; - bunaen, ie in the above i'oriiiel V is f = O or 1. In the 3-di oils en sir.d äementscrecliend cie hydroxyl groups r: nv; eixesten separated from each other. 2s' .. "uröe found, ar.I Uiole, in which the hy5rox; en veiter v ^ no? -näor are removed, aie superior faithfulness. the erfincr.n .s t: einä.i; do not own en liole. Vieiraehr have diols with v. ?. T - i "; he another, distant hydroxygruop'en the Li ^ s & chef th EINV r erti he jiikonole which, as below 6 ec isplays v; ith the erfindun ^ sgeitE-iei: α- and ß.. Dioleii v: eit unt;: rle t : eii cind.
Das i).iol mui: r;:indeeter.s 10 vnä \ro:.'."u^Bv;eise ι.:ίηαεετ;εηε i2 Kohlenstoffrtoine txit!:; Iten. 3s '.τιroe gefunäen, öi-.J- Uiole mit weniger eis 10 Kohlenstoffatomen nicht die überlegenen Antiabnutzunts- und öchnitreigeiiooh?.i'ten der C^Q-C-Q-Liole auf v/eisen. Die Diole mit einer niedrigeren Kohlensto: f r:r.hl haben etv/a die bleichen ociimiereigenschaften v/ie die einwertigen C-jQ-OvQ alkohole. Ähnlich wurde ^efrmden, äc,ü die Diole mit mehr elf.. 30 Koi.lenstol'fatoraen den 0-^-0^0 Diolen nicht äquivi-i'jijt'sind.Das i) .iol mui: r;: indeeter.s 10 vnä \ r o:. '. "U ^ Bv; eise ι.: Ίηαεετ; εηε i2 Carbon txit!:; Iten. 3s ' .τιroe gefunänen, öi- .J- Uiols with less than 10 carbon atoms do not have the superior anti-wear and tear-resistant properties of the C ^ QCQ-Liole on iron. The diols with a lower carbon: fr: r.hl have etv / a the pale ones . not 0 ^ 0 diols äquivi-i'jijt '- ociimiereigenschaften v / ie the monovalent C-jQ-OVQ alcohols Similarly ^ was efrmden, AEC, the diols ü with more eleven .. 30 Koi.lenstol'fatoraen the 0 - ^ are.
1 09 8-1 Π / 2.0 11 09 8-1 Π / 2.0 1
BAO ORiGtNALBAO ORiGtNAL
2U42279.2U42279.
Die Trägerflüseigkeit, die den größeren Anteil des erfin- ciungsgemäßen Schmiermittels ausmacht, kann ein Mineralöl, ein Kohlenwasserstofföl, ein Kohlenwasserstoffdestillat, ein halor:enierter/oxygenierter Kohlenwasserstoff oder l/asser sein. Wasser v.'ird wegen seiner hohen >.<arme ableitung eis l'ragerflüssigkeit bevorzugt. Wenn V/ass-er als Trägcrflüssigkeit verwendet wird, bevorzugt man,eine kleine Menge, im allgemeinen bis zu etwa 5 his 10 Volum^ eines Emulgiermittels zvl dem -.,asser-Diol Gemisch zu geben. Das Emulgiermittel icann ionisch oder nicht-ionisch sein. Geeignete Emulgiermittel sind Alkylarylpolyäthoxyalkohole, Sorbitanmonooleat, polyäthoxylierte Amine, Amide oder Fettsäuren, Zukkerester, Seifen und Sulfonate.The Trägerflüseigkeit, which accounts for the greater proportion of the inventions ciungsgemäßen lubricant, a mineral oil, a hydrocarbon oil, a hydrocarbon distillate, a halo r can: enierter / oxygenated hydrocarbon or l / ater be. Water v. Is preferred because of its high>. <Poor drainage ice l'rageriquid. When using as a carrier liquid, it is preferred to add a small amount, generally up to about 5 to 10 volumes, of an emulsifying agent to the water-diol mixture. The emulsifier can be ionic or non-ionic. Suitable emulsifiers are alkylaryl polyethoxy alcohols, sorbitan monooleate, polyethoxylated amines, amides or fatty acids, sugar esters, soaps and sulfonates.
Als Trägerflüssigkeiten für die erfindun..sgemäßen Zwecke geeignete Öle sind im allgemeinen Kohlenwasserstofföle, die durch Destillation, Cracken, Hydrierung oder a.näere Refining-Verfahren hergestellt werden. Sie haben typische Siedepunkte von 260 bis 540° C und Viskositäten von 50 bis 500 SSU bei 38° C. Jiin typisches Beispiel für ein geeignetes Ol ict ein neutrales Kohlenwasserstofföl mit einer·Viskosität von 130 SbU bei 38° 0. Sie können zu einem kleineren Teil selbst zur Schmierung beitragen.As carrier liquids for the purposes according to the invention suitable oils are generally hydrocarbon oils, those by distillation, cracking, hydrogenation or similar Refining process are produced. You have typical Boiling points from 260 to 540 ° C and viscosities from 50 to 500 SSU at 38 ° C. Jiin typical example of a suitable Oil is a neutral hydrocarbon oil with a viscosity of 130 SbU at 38 ° 0. You can go to a smaller one Part itself contribute to the lubrication.
ebenfalls geeignet als Trägerflüssigkeiten sind halogenierte und oxygenierte Kohlenwasserstoffe. Sie werden insbesondere als Trägerflüssigkeiten für die a-Diole bevorzugt, denn letztere hat.en-in diesen Kicht-Kohlenwasserstoffflüssigkeiten oft eine größere Löslichkeit als in ο en Kohlenwasserst off flüssigkeit en.Halogenated ones are also suitable as carrier liquids and oxygenated hydrocarbons. They are particularly preferred as carrier liquids for the a-diols because the latter has.en-in these non-hydrocarbon liquids often a greater solubility than in ο en hydrocarbons off liquid en.
Zu den erfindungsgemäß -brauchbaren oxygenierten Kohlenwassersto-^flüssigkeiten gehören Carbonsäureester, Alkohole, Ketone, Äther und Aldehyde. Die hnlogensubstituierten Kohlenwasserstoffe umfassen Halogenalk.yl- und Halogenarylkoh-To the oxygenated hydrocarbon liquids that can be used according to the invention include carboxylic acid esters, alcohols, ketones, ethers and aldehydes. The similarly substituted hydrocarbons include haloalk.yl- and haloarylkoh-
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lenwasserstoffe. Die flüssigen Träger können "beide Substituenten aufweisen, wie im Falle eines Halogenäthers. Typische verwendbare Ficht-Kohlenwasserstoffflüssigkeiten sind Tetrachlorkohlenstoff, 1,1,1-Trichloräthan, Chloroform, Bromoform, 1,2-Dichloräthan, Chlorbenzol, Äthanol, Metha-. nol, Isopropanol, Allylalkohol, Benzylalkohol, n-Butyraläehyd, Benzaldehyd, Aceton, Methyläthylketon, 2-Hexanon, Methylisobutylketon, Xthyläther, n-Propyläther, Äthylphenyläther, 1,4—Dioxan und Propylenoxid.hydrocarbons. The liquid carriers can "have both substituents have, as in the case of a halogen ether. Typical spruce hydrocarbon liquids that can be used are Carbon tetrachloride, 1,1,1-trichloroethane, chloroform, Bromoform, 1,2-dichloroethane, chlorobenzene, ethanol, metha-. nol, isopropanol, allyl alcohol, benzyl alcohol, n-butyralehyde, Benzaldehyde, acetone, methyl ethyl ketone, 2-hexanone, Methyl isobutyl ketone, ethyl ether, n-propyl ether, ethylphenyl ether, 1,4-dioxane and propylene oxide.
Die obigen Materialien sind nur als Beispiele angegeben. Es kann jeder geeignete Kohlenwasserstoff, halogenierte Kohlenwasserstoff oder oxygenierte Kohlenwasserstoff verwendet werden, der durch Anwendung geeigneter Emulgiermittel mit dem besonderen in Frage stehenden α- oder ß-Diol mischbar gemacht werden kann. Außerdem kann die "Trägerflüssigkeit" aus einer Mischung von zwei oder mehreren der obigen Materialien bestehen. Alle in dieser Weise miteinander kombinierten Materialien sollten gegenseitig mischbar sein oder durch die Verwendung geeigneter Emulgiermittel mischbar gemacht werden können.The above materials are given as examples only. It can be any suitable hydrocarbon, halogenated Hydrocarbon or oxygenated hydrocarbon can be used by applying suitable emulsifying agents with the particular alpha or beta diol in question can be made mixable. In addition, the "carrier liquid" can be a mixture of two or more of the above Materials exist. All materials combined in this way should be mutually miscible or can be made miscible through the use of suitable emulsifying agents.
In der erfindungsgemäßen Schmiermittelzusammensetzung macht { das Diol den kleineren Anteil aus. In typischer Weise stellt das Diol nicht mehr als 30 Vol.^ des Diol-Trägerflüssigkeit Gemisches. Vorzugsweise macht das Diol nicht mehr als 15 Vol.$ des Gemisches aus und insbesondere nicht mehr als 10 Vol.$. Die kleinste Diolkonzentration ist 0,1 Vol.$. Wach einer bevorzugten Ausführungsform wird das Diol zuerst in einem Polyolefin dispergiert, z.B. Polybuten mit einem Zahlenmittel des Molekulargewichts von etwa 300 bis 1000. Das Gemisch wird dann in Wasser emulgiert. Diese Materialien werden während des auf das Kaltwalzen des Aluminiums folgenden Abkühlens leicht verflüchtigt und lassen so auf dem Aluminium nur einen geringen Oberflächenrückstand zurück. Im allge- In the lubricant composition of the present invention, the diol makes up the minor portion. Typically, the diol constitutes no more than 30 vol. ^ Of the diol-carrier liquid mixture. Preferably the diol makes up no more than 15% by volume of the mixture, and more preferably no more than 10% by volume. The smallest diol concentration is 0.1 vol. $. In a preferred embodiment, the diol is first dispersed in a polyolefin, for example polybutene having a number average molecular weight of about 300 to 1000. The mixture is then emulsified in water. These materials are easily volatilized during the cooling following the cold rolling of the aluminum, leaving little surface residue on the aluminum. In general
109 8 10/201B109 8 10 / 201B
2U422792U42279
- ίο -- ίο -
meinen beträgt das Volumverhältnis von Diöl zu Polyolefin 1:1 "bis 1:10. In einer ty^it.chen erfinaungsgemäßen Zusammensetzung sind 90 Vol.yj Wasser, 2 Vol.;' Diol, 7,5 Vol.;/:- Polybuten und 0,5 Vol.;o nicht-ionische Emulgiermittel enthalten. mine is the volume ratio of di-oil to polyolefin 1: 1 "to 1:10. In a typical composition according to the invention are 90 vol.yj water, 2 vol .; ' Diol, 7.5 vol .; /: - Polybutene and 0.5 vol.; O contain non-ionic emulsifiers.
Die erfindungsgemäße Schmiermittelzusammensetzung kann cmch herkömmliche Zusätze enthalten, z.B. !Rostschutzmittel, Oxydationsinhibitoren und Schmiermittel. Ein typisches Schmiermittel ist Specköl. Diese Zusätze sind normalerweise in einer Menge von 5 bis 25 Gew.^ des Schmiermittels vorhanden. The lubricant composition of the invention may contain c mch conventional additives, for example! Rust inhibitors, oxidation inhibitors and lubricants. A typical lubricant is lard oil. These additives are normally present in an amount of from 5 to 25 percent by weight of the lubricant.
Die Tabelle I erläutert die Schmiereigenschaften der erfindungsgemäßen Diol-Schmiermittel. Die Daten dieser Tabelle wurden in einem "Falex Maschinen" Test erhalten. Dieser Test, bei dem eine zylindrische Stahlwelle zwischen und in Kontakt mit zwei V-förmigen Aluminiumblöcken rotiert, ist bekannt. Die Welle ist über einen kleinen Scherbolzen mit einem Motor verbunden. Die Welle und die Blöcke tauchen in das zu testende Schmiermittel ein. Die Blöcke werden zunehmend belastet, so daß sie gegen die Welle gedrückt werden. Der Punkt, an dem die Welle sich an den Blöcken festläuft und den Scherbolzen abschert, wird gemessen und die auf die Blöcke ausgeübte Belastung in kg an diesem Punkt als Ausfallbelastung des Schmiermittels aufgezeichnet.Table I illustrates the lubricating properties of the invention Diol lubricant. The data in this table were obtained in a "Falex machine" test. This test, in which a cylindrical steel shaft between and rotating in contact with two V-shaped aluminum blocks is known. The shaft is over a small shear bolt connected to an engine. The shaft and blocks are immersed in the lubricant to be tested. The blocks will increasingly loaded so that they are pressed against the shaft. The point at which the shaft meets the blocks sticks and shears the shear bolt is measured and the load in kg on the blocks at that point recorded as the failure load of the lubricant.
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2ÜA2 27 92ÜA2 27 9
DiolDiol
konzentration im Scrmiermittel,Vol.>ö concentration in the lubricant, vol.> ö
Λϋ äs sr ige l'rägerf lüssigkei t
1 ,2-iiexadecanäiol
1 , 2-üodecs.nüiol
1 ,2-(G1 c-C1ö)Alkcinüiol-Hischung As a liquid carrier liquid 1, 2-iiexadecanäiol
1, 2-üodecs.nüiol
1, 2- (G 1 cC 10 ) alkcinol mixture
1 , 3-Alketnäiol liischung ?us C1P5-C18 Olefinen1,3-Alketnäiol liigung? From C 1 P 5 -C 18 olefins
kohlenwasserstoff-Trägerflüs-hydrocarbon carrier fluid
si;:keitsi;: speed
1,2-(C1 K-C1..) alkandiol-Hi-1,2- (C 1 K -C 1 ..) alkanediol-Hi-
1,2-(C1-C16) Uic
schung1,2- (C 1 -C 16 ) Uic
schung
1,3-Alkandiol-Mischung aus1,3-alkanediol mixture of
C-Ir-C1Q Olefinen
Ί 5 IoC-Ir-C 1 Q olefins
Ί 5 Io
1 ,3-Alkanäiol-i-Iischung fus C1C-C18 Olefinen1,3-Alkanäiol-I-I-I-mixture for C 1 CC 18 olefins
2-(1'-Hydrοχy üthyl)-4-2- (1'-Hydrοχy üthyl) -4-
(C1 (--C oQalkyl)-c— me thylphenol-(C 1 (--C oQalkyl) -c- methylphenol-
Hi schungHi schung
2-(1'-Hyäroxyäthyl)-4-( 1",3" , 5" , 7"-tetramexhTloctj7"!)phenol2- (1'-hydroxyethyl) -4- (1 ", 3", 5 ", 7" -tetramexhTloctj 7 "!) Phenol
2 22 2
1 5 11 5 1
Falex-Ausfallbelastung, kgFalex failure load, kg
1 820 1 b20 1 3851 820 1 b20 1 385
820820
1 1351 135
Aus den Daten der Tabelle I ist ersichtlich, daß eine Vielzahl von α- und ß-Diolen :"ür die erfindungsgemäßen Zwecke brauchbar ist. Die erhaltenen V/erte zeigen ferner, daß eine gute Schmierung erzielt wird, unabhängig davon, ob die SchmieriTüssig;--ceit, in der die Diole dispergiert sind, wässrig oder nicht wässrig ist.It can be seen from the data in Table I that a large number of of α- and ß-diols: "for the purposes according to the invention is useful. The values obtained also show that one good lubrication is achieved regardless of whether the Lubricating liquid; - the time in which the diols are dispersed, aqueous or is not watery.
Die Tabelle II erläutert die Überlegenheit der α- und ß-Diole gegenüber ähnlichen Materialien, wie Diolen, bei denen die Hydroxylgruppen weit voneinander entfernt sind,oderTable II illustrates the superiority of the alpha and beta diols to similar materials, such as diols, in which the hydroxyl groups are far apart, or
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einwertigen Alkoholen. Alle in der nachfolgenden Tabelle aufgeführten Materialien waren in einer Menge von 2 Vol.'i nes v/ässrigen Schmiermittels vorhanden.monohydric alcohols. All in the table below materials listed were in an amount of 2 vol No aqueous lubricant available.
Aus den Daten der Tabelle II ist ersichtlich, daß die a- und ß-Mole in ihren Schmiereigenscheften allen anderen aufgeführten Verbindungen weit überlegen sind, nahe verwandte Verbindungen, wie Diole, in denen die Hydroxylgruppen weiter voneinender entfernt sind und einwertige Alkohole eingeschlossen. From the data in Table II it can be seen that the a- and ß-moles in their greasy properties of all others listed compounds are far superior to closely related compounds, such as diols, in which the hydroxyl groups continue are distant and include monohydric alcohols.
Die erfincungsgemäß verwendeten Diole haben, wenn sie als Aluminiumschmiermittel verwendet werden, auch ausgezeichnete Antiabnutzungseigenschaften. Daß sie den entsprechenden einwertigen Alkoholen in dieser Him-;icht weit überlegen sind, geht aus eier Tabelle III hervor. Die werte dieser Tabelle wurden in einem modifizierten "Falex iiaachinen"The diols used according to the invention have when they are used as Aluminum lubricants are used, also have excellent anti-wear properties. That they are the appropriate monohydric alcohols in this mind; ot far superior are shown in Table III. The values of this Table were modified in a "Falex iiaachinen"
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2 Ü 4 2 2 7 92 nights 4 2 2 7 9
Test erhalten. In diesem modifizierten Test wurde eine-konstante Kraft a.uf die Aluminiumblöcke ausgeübt. Die Stahlwelle rotierte eine bestimmte Zeit zwischen diesen Blöcken. ¥ach Ablauf dieser Zeit wurde die von den Blöcken abgeriebene Menge Aluminium festgestellt und der Aluminiumverlust in mg aufgezeichnet.Test received. In this modified test, a -constant Force exerted on the aluminum blocks. The steel shaft rotated a certain time between these blocks. After this time, the one rubbed off the blocks The amount of aluminum was determined and the aluminum loss recorded in mg.
tion im
Schmiermit
tel, Vol.;*Concentration
tion in
Lubricant
tel, vol.; *
abrieb, mgaluminum
abrasion, mg
sigkeitHydrocarbon carrier fluid
sweetness
2-(1'-Hydroxyäthyl)-4-2- (1'-hydroxyethyl) -4-
(O1CT-G9n —alkyl)-6~methylphenol-(O 1 CT-G 9n -alkyl) -6-methylphenol-
MisdhufMisdhoof
2-(i'-Hydroxyäthyl)-4-(T",3", 5"^"-tetramethyloctyljphenol2- (i'-hydroxyethyl) -4- (T ", 3", 5 "^" - tetramethyloctylphenol
13 1113 11
Aus den Daten der Tabelle III ist ersichtlich, daß die a- und ß-Diole in ihren Antiabnutzungseigenschaften den verwandten Materialien weit überlegen sind. From the data of Table III that the a- and ß-diols char acteristics in their antiwear be seen, the related materials are far superior.
In einem weiteren Test wurde ein Schmiermittel für die maechinelle Bearbeitung von Aluminium aus 80 Gew.$ 1,1,1-Trichloräthan, 16 Gew.# Speoköl, 4 Gew.# 1,2-(C15-Cj8)-Allcandiol-Mischung und einem kleinen Zusatz eines G-eruchastof-In another test, a lubricant for the processing of aluminum maechinelle was of 80 wt. $ 1,1,1-trichloroethane, 16 wt. # Speoköl, 4 wt. # 1,2- (C 15 -CJ 8) -Allcandiol- Mixture and a small addition of a G-eruchastof-
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-H--H-
fes hergestellt. Dieses Schmiermittel wurde für das G-ewindeschneiden von Aluminium verwendet. Es wurde gefunden, daß die Lebensdauer des G-ev/inde Schneiders um mehr als das Zehnfache über die Lebensdauer (d.h. die Zeit bis zum Brechen des G-ewindeschneiders) erhöht wurde, die man mit dem gleichen Schmiermittel erhielt, in dem jedoch kein Diol enthalten war.fes made. This lubricant was made for thread cutting used by aluminum. It has been found that the life of the G-ev / inde cutter is more than ten times over the service life (i.e. the time until the thread cutter breaks) that one with the same Lubricant received, but in which no diol was included.
Die erfindungsgemäß verwendeten Diole sind z.T. im Handel erhältlich. In anderen Fällen können sie synthetisiert werden. Synthesen für tycische α- und Ö-Diole sind nachfolgend beschrieben.Some of the diols used according to the invention are commercially available available. In other cases they can be synthesized. Syntheses for typical α- and Ö-diols are given below described.
Sine Mischung aus 245 g (1 Mol) "ITedox 1518", einem im Handel erhältlichen Gemisch aus endständigen C^-C^q Epoxyden, hergestellt aus gecrackten Wachs-Olefinen und vertrieben von der Ashland Oil and Refining Co., 90 g (5 Mol) "Wasser und 2 g konzentrierter Schwefelsäure als Katalysator wurden 8 Stunden bei 100° 0 unter Rückfluß erhitzt, säurefrei gewaschen und getrocknet. Das Produkt bestand aus einem wachsartigen weißen Peststoff; P = 52° C, das 1,2-(C15-C18)-Alkandiole enthielt.A mixture of 245 g (1 mole) of "ITedox 1518", a commercially available mixture of C ^ -C ^ q terminal epoxies, made from cracked wax olefins and sold by Ashland Oil and Refining Co., 90 g Mol) "Water and 2 g of concentrated sulfuric acid as catalyst were refluxed for 8 hours at 100 ° 0, washed acid-free and dried. The product consisted of a waxy white pesticide; P = 52 ° C, the 1,2- (C 15 -C 18 ) alkanediols.
Nach dem Verfahren des Beispiels 1 wurde unter Verwendung von 1,2-Epoxydodecan 1,2-Dodecandiol hergestellt} P = 53° C.Following the procedure of Example 1 using 1,2-epoxydodecane, 1,2-dodecanediol was prepared} P = 53 ° C.
Nach dem Verfahren des Beispiels 1 wurde unter Verwendung von 1,2-Epoxyhexadecan 1,2-Hexadecandiol hergestellt! P = 49° C. Following the procedure of Example 1 using 1,2-epoxyhexadecane, 1,2-hexadecanediol was prepared! P = 49 ° C.
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'-■.ine Lösung aus 270 g (1 Hol) eines Gemisches von gecrackten C-io-CpQ Wachs-ülefinen, 30 g (1 KoI) Paraformaldehyd, 120 j? (2 kol) Essigsäure und 30 g Schwefelsäure als katalysator wurde ZA Stunden auf 100 bis 120 C erhitzt, dann mit verdünnter iiauB-Lösung und '-,/asser gewaschen. Die erhal tenen rohen Ester wurden mit KOE-Lösung zu einem Gemisch aus 1 ,3-(C1O-C.-J0)Alkaneiolen umgesetzt.A solution of 270 g (1 ha) of a mixture of cracked C-io-CpQ wax olefins, 30 g (1 KoI) paraformaldehyde, 120%? (2 kol) of acetic acid and 30 g of sulfuric acid as catalyst ZA hours was heated to 100 to 120 C, then with dilute iiauB solution and '-, / ater washed. The crude esters obtained were reacted with KOE solution to form a mixture of 1,3 (C 1 OC.-J 0 ) alkanols.
Aus den ooigen Ausführungen geht hervor, daß die α- und a-Diole soga.r in sehr geringen Konzentrationen überlegene Aluminiumschmiermittel und Antiabriebzusätze darstellen. Sie haben eine höhere Belastungskepazität und vermögen die Aluminiumabnutzung stärker zu verringern.From the ooigen versions shows that the α- and a-diols represent soga.r in very low concentrations superior aluminum lubricants and anti-wear additives. They have a higher load capacity and are able to reduce the aluminum wear and tear to a greater extent.
BAD ORIGINAL 1098 10/201 BBAD ORIGINAL 1098 10/201 B
Claims (12)
IOH
I.
C
(R4)(R 3 ),
C.
(R 4 )
in der R eine aliphatische Kohlemvasserstoffgruppe1 '
in which R is an aliphatic hydrocarbon group
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US85347469A | 1969-08-27 | 1969-08-27 | |
US88880669A | 1969-12-29 | 1969-12-29 |
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Publication Number | Publication Date |
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DE2042279A1 true DE2042279A1 (en) | 1971-03-04 |
Family
ID=27127147
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19702042279 Pending DE2042279A1 (en) | 1969-08-27 | 1970-08-26 | Method of lubricating aluminum and aluminum alloys |
Country Status (10)
Country | Link |
---|---|
US (1) | US3649538A (en) |
JP (1) | JPS4827868B1 (en) |
BE (1) | BE754672A (en) |
CA (1) | CA923488A (en) |
CH (1) | CH567566A5 (en) |
DE (1) | DE2042279A1 (en) |
FR (1) | FR2059697B1 (en) |
GB (1) | GB1288879A (en) |
NL (1) | NL7012714A (en) |
SE (1) | SE362658B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2439815A1 (en) * | 1978-10-27 | 1980-05-23 | Pennwalt Corp | METHOD FOR REDUCING THE RESIDUES OF NON-VOLATILE CARBON PRODUCTS RESULTING FROM THE TREATMENT, AT HIGH TEMPERATURE, OF A METAL SUBSTRATE WITH A TREATMENT COMPOSITION |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3855136A (en) * | 1971-11-15 | 1974-12-17 | Kaiser Aluminium Chem Corp | Dispersion for hot rolling aluminum products |
US3755168A (en) * | 1971-12-03 | 1973-08-28 | Phillips Petroleum Co | Lubricant for extrusion of thermoplastics |
US3846319A (en) * | 1973-03-27 | 1974-11-05 | Chevron Res | Dioxan-containing aluminum lubricant |
US4331222A (en) * | 1980-07-07 | 1982-05-25 | Chevron Research Company | Method for reducing brake noise in oil-immersed disc brakes |
DE3035016C2 (en) * | 1980-09-12 | 1985-02-21 | Schweizerische Aluminium Ag, Chippis | Oil-in-water emulsion for cold rolling light metals |
US4406803A (en) * | 1980-11-24 | 1983-09-27 | Chevron Research Company | Method for improving fuel economy of internal combustion engines |
US4371447A (en) * | 1981-07-06 | 1983-02-01 | Standard Oil Company | Low viscosity water-in-oil microemulsions |
US4927553A (en) * | 1983-05-06 | 1990-05-22 | Ethyl Corporation | Haze-free boronated antioxidant |
US4632771A (en) * | 1984-08-17 | 1986-12-30 | Chevron Research Company | Normally liquid C14 to C18 monoalkyl catechols |
US4704218A (en) * | 1985-12-16 | 1987-11-03 | Horodysky Andrew G | Reaction products of sulfur containing vicinal diols and hydrogen phosphites as lubricant and fuel additives |
US4781848A (en) * | 1987-05-21 | 1988-11-01 | Aluminum Company Of America | Metalworking lubricant comprising an oil-in-water microemulsion |
US4781849A (en) * | 1987-05-21 | 1988-11-01 | Aluminum Company Of America | Lyotropic liquid crystal metalworking lubricant composition |
US6004911A (en) * | 1995-12-27 | 1999-12-21 | Denso Corporation | Processing oil suitable for aluminum materials and removable via heating |
JP5441480B2 (en) * | 2009-04-10 | 2014-03-12 | 昭和シェル石油株式会社 | Lubricating oil composition |
US10844264B2 (en) | 2015-06-30 | 2020-11-24 | Exxonmobil Chemical Patents Inc. | Lubricant compositions comprising diol functional groups and methods of making and using same |
US20170002251A1 (en) | 2015-06-30 | 2017-01-05 | Exxonmobil Chemical Patents Inc. | Glycerol Carbamate Based Lubricant Compositions and Methods of Making and Using Same |
US10927283B2 (en) | 2016-12-28 | 2021-02-23 | Exxonmobil Chemical Patents Inc. | Friction-reducing compositions for use in drilling operations |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB629139A (en) * | 1947-06-23 | 1949-09-13 | Shell Refining & Marketing Co | Improvements in or relating to emulsification and emulsifying compositions |
US3400083A (en) * | 1964-07-10 | 1968-09-03 | Exxon Research Engineering Co | Lubricating films |
-
1969
- 1969-12-29 US US888806A patent/US3649538A/en not_active Expired - Lifetime
-
1970
- 1970-07-14 CA CA088179A patent/CA923488A/en not_active Expired
- 1970-07-31 CH CH1162170A patent/CH567566A5/xx not_active IP Right Cessation
- 1970-08-10 BE BE754672A patent/BE754672A/en not_active IP Right Cessation
- 1970-08-19 FR FR7030440A patent/FR2059697B1/fr not_active Expired
- 1970-08-24 GB GB4071970A patent/GB1288879A/en not_active Expired
- 1970-08-24 SE SE11468/70A patent/SE362658B/xx unknown
- 1970-08-24 JP JP45073557A patent/JPS4827868B1/ja active Pending
- 1970-08-26 DE DE19702042279 patent/DE2042279A1/en active Pending
- 1970-08-27 NL NL7012714A patent/NL7012714A/xx not_active Application Discontinuation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2439815A1 (en) * | 1978-10-27 | 1980-05-23 | Pennwalt Corp | METHOD FOR REDUCING THE RESIDUES OF NON-VOLATILE CARBON PRODUCTS RESULTING FROM THE TREATMENT, AT HIGH TEMPERATURE, OF A METAL SUBSTRATE WITH A TREATMENT COMPOSITION |
Also Published As
Publication number | Publication date |
---|---|
FR2059697A1 (en) | 1971-06-04 |
CH567566A5 (en) | 1975-10-15 |
SE362658B (en) | 1973-12-17 |
US3649538A (en) | 1972-03-14 |
NL7012714A (en) | 1971-03-02 |
CA923488A (en) | 1973-03-27 |
FR2059697B1 (en) | 1974-08-23 |
GB1288879A (en) | 1972-09-13 |
BE754672A (en) | 1971-01-18 |
JPS4827868B1 (en) | 1973-08-27 |
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