CS274074B1 - Method of multi-functional admixture production into lubricating oils on base of zinc dialkyl dithiophosphate - Google Patents
Method of multi-functional admixture production into lubricating oils on base of zinc dialkyl dithiophosphate Download PDFInfo
- Publication number
- CS274074B1 CS274074B1 CS321789A CS321789A CS274074B1 CS 274074 B1 CS274074 B1 CS 274074B1 CS 321789 A CS321789 A CS 321789A CS 321789 A CS321789 A CS 321789A CS 274074 B1 CS274074 B1 CS 274074B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- zinc
- base
- lubricating oils
- production
- dialkyl dithiophosphate
- Prior art date
Links
- 229910052725 zinc Inorganic materials 0.000 title claims abstract description 18
- 239000011701 zinc Substances 0.000 title claims abstract description 18
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- 239000010687 lubricating oil Substances 0.000 title abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- -1 saturated aliphatic alcohols Chemical class 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 239000011593 sulfur Substances 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 12
- 230000000996 additive effect Effects 0.000 claims description 11
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract description 6
- 238000006386 neutralization reaction Methods 0.000 abstract description 5
- 150000003752 zinc compounds Chemical class 0.000 abstract description 3
- 239000005864 Sulphur Substances 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- 230000008021 deposition Effects 0.000 description 2
- 239000003879 lubricant additive Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- VVQDPBBEEQETOE-UHFFFAOYSA-N 2-ethyl-2-methyloxane Chemical compound CCC1(C)CCCCO1 VVQDPBBEEQETOE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 101100478330 Rattus norvegicus Srgn gene Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
Landscapes
- Lubricants (AREA)
- Catalysts (AREA)
Abstract
Description
Vynález sa týká sposobu výroby multifunkčnej přísady do mazacích olejov na báze dialkyldltiofosforečnanu zinočnatého. Rieši spás ob výroby multifunkčnej přísady do maziv na báze dialkyldltiofosforečnanu zinočnatého raakciou naeýtených alifatických alkoholov dťžkou reťazoa od do eo aímikom fooforečným v prítomnooti volnej a/ alebo elementárnej siry a dodatočnou neutrallzáoiou bazickou zinočnatou zlúčeninou.The present invention relates to a process for the production of a zinc dialkyldiophosphate multifunctional lubricant oil additive. It resolves the production of a multifunctional lubricant additive based on zinc dialkyldiophosphate by the reaction of saturated aliphatic alcohols with chain lengths of from about to about 10% in the presence of free and / or elemental sulfur and an additional neutral zinc compound with basic zinc.
Podía doteraz známých postupov, pri příprava dialkyldltiofosforečnanu zinočnatého z Jodnotlivýoh alebo zmesnýcb allfatiokýoh alkoholov až C12 80 eírnikom fosforečným pri teplote 60 až 110 °C a po dodatočnej neutralizácii e oxidom, resp, hydroxidom zinočnatým pri teplota 40 až 80 °C vzniká produkt s poměrně nízkým výťažkom, často s nevyhovujúclmi kvalitatívnými vlastnostami.According to the known processes, in the preparation of zinc dialkyldiophosphate from iodine or mixed aliphatic alcohols up to C 12 80 by phosphorous at 60 to 110 ° C and after additional neutralization with zinc oxide or zinc hydroxide at a temperature of 40 to 80 ° C low yield, often with unsatisfactory quality characteristics.
Zlepšenie kvalitatívnyoh vlaatnoatí, zvýšenie výtažku dialkyldltiofoaforečnanů zinočnatého podťa známých postupov možno dosiahnút použitím vhodného katalyzátore, iniciátora, príp. ultrazvuku pri příprava. Raakoiu sírnika fosforečného s elkoholmi katolyzujú zlúčoniny typu Me^PO, Me^PS, Me^HCl, Bu^PBr, MegP/S/SNa podťe/Ger. Offen 3 011 085/, aoetály a metyletyltetrahydropyrán podlá /DD pat, 201 146/j H^PO^ a’jej kovové soli, HjSO^ a voda podťa /UŠ pat. 4 681 964/. Na reakclu sa používajú katalyzátory v množstvo 2 až 25 % hmot.Improvement of qualitative swelling, increase of zinc dialkyldiophosphate yield according to known processes can be achieved by using a suitable catalyst, initiator, resp. ultrasound preparation. Raakoiu phosphorus pentasulfide with alcohols are catalyzed by compounds of the type Me4 PO, Me4 PS, Me4 HCl, Bu4 PBr, MegP / S / SN and Pod / Ger. Offen 3 011 085], etetals and methylethyltetrahydropyran according to (DD Pat, 201 146), its metal salts, H 2 SO 4 and water according to US Pat. 4,681,964 /. 2 to 25 wt.% Catalysts are used for the reaction.
Tieto nedostatky sú odstránené u výroby multifunkčnej přísady do maziv na báze dialkyldltiofosforečnanu zinočnatého raakciou naeýtených alifatických alkoholov so sírnikom fosforečným pri teplote 80 až 110 °C a následnou neutrallzáoiou s bazickou zinočnatou zlúčeninou pri teplota 60 až 100 °C podťa vynálezu, ktorého podstatou ja, že reakcia naeýtených alifatických alkoholov dťžkou reťezoe až so sírnikom fosforečným sa uskutočňuje v přítomnosti volnaj síry obsiahnutej v PgS^ a/ alebo elementárnej síry v množstve 3,5 až 4,1 % hmot. na síraik fosforečný.These drawbacks are eliminated in the production of a multifunctional lubricant additive based on zinc dialkyldiophosphate by the reaction of saturated aliphatic alcohols with phosphorus pentasulfide at a temperature of 80 to 110 ° C and subsequent neutrallization with a basic zinc compound at a temperature of 60 to 100 ° C according to the invention. the reaction of the saturated aliphatic alcohols with a chain length up to phosphorus sulphide is carried out in the presence of free sulfur contained in PgS2 and / or elemental sulfur in an amount of 3.5 to 4.1% by weight. to phosphorus pentasulfide.
Výhodou uvedeného spásobu riešenia je zvýšenie výťažku dialkyldltiofosforečnanu zinočnatého pri vyhovujúcich kvalitatívnyoh vlastnostiach prísedy z hťadiska obsahu P, S, Zn, negativného korozívneho posobenie na Cu podťa ASTM a zlepšení vzhíadu z hťadiska Čirosti.The advantage of said method is to increase the yield of zinc dialkyldiophosphate at satisfactory qualitative properties of the additive in terms of P, S, Zn content, negative corrosive deposition on Cu according to ASTM and to improve the appearance in terms of clarity.
Kvalitná přísada dialkyldltiofosforečnanu zinočnatého má obsahovať okrem normálnej aj bazická soť zinku, čo často sposobuje ťažkosti pri výroba a následná pri čistění přísady. Ďalšou výhodou spčfeobu výroby podťe vynálezu Je, že v stupni neutralizácie je možné zabezpečit* dostatočný poměr bazlckej a normálnej soli dialkylditlofosforečnanu zinočnatého bez vplyvu na čTalšie spracovateťské vlastnosti týkajúce se čistenia přísady, hlavna filtráciou.A high-quality zinc dialkyldiophosphate additive should contain, in addition to normal, a basic zinc salt, which often causes difficulties in production and subsequent cleaning of the additive. A further advantage of the process according to the invention is that in the degree of neutralization it is possible to ensure a sufficient ratio of basal to normal zinc dialkyl phosphate salt without affecting the further processing properties of the additive purification, in particular by filtration.
Všeobecne PgS^, vhodný na výrobu přísad, obsahuje rázné množetvo volnej síry, ktoré sa stanovuje hydrolytickou metodou. Obsah volnej síry v sirníku fosřoračnom podmlaňuje jaho spraoovateťskó vlastnosti, Menej ako 3,5 % hmot. voťnej eíry v PgS^ pri reakcil a elkoholmi sposobuje ťažkosti pri neutralizácii a filtráoli přísady, Podťa ziatanej hmotnosti voťnej síry v PgS^ podťa vynálezu, na reakclu s elkoholmi sa doplňa elamantárna síra, čisto™ 99.8 % hmot,, v množstve 3,5 až 4,1 % hmot. na P2S^. Při vačšom množstva voťnej eíry v P^S^ ako 4,1% hmot.,vyrobený produkt má korozívne účinky na Cu podťa ASTM. Podťa uvedeného sposobu riešenia vtedy sa aíraik upravuje zmiešaním dvooh alebo viao druhov PgS^, 0 vyšším a nižším obsahom voťnej aíry tak, aby výsledná zmes obsahovala určené množstvo volnej síry, a/ alebo chýbajúce množstvo doplnilo elementárnou sírou. Výhodou uvedeného spdsobu riešenia podťa vynálezu Je, že možno zabezpečit’ yhodné epracovatelskó vlastnosti rázných sírnikov fosforečných a vyhovujúce kvalitativně vlastnosti získanej přísady.In general, the PgS ^ suitable for the preparation of additives contains a vigorous amount of free sulfur, which is determined by the hydrolysis method. The free sulfur content of the phosphorus sulfide undermines its management properties, less than 3.5% by weight. The amount of free sulfur in PgS4 in the reagents and the alcohols causes difficulties in neutralization and filtration of the additive. 4.1 wt. to P 2 S ^. The greater amount of the loose much of the Irish P ^ S ^ than 4.1 wt.%, The product produced is corrosive to the wire sub-theme available. Sub-topic of the process solution if the aíraik provides for mixing or dvooh viao species PgS ^ 0 the higher and lower vötn The sulfur such that the resulting mixture contains the specified amount of the free sulfur and / or complement the missing amount of elemental sulfur. It is an advantage of the method according to the invention that the epoxy processing properties of the phosphorus sulphide can be identical and that the properties of the additive obtained are satisfactory.
Vynález je bllžšle objasněný na ďalej uvedenýoh príkladooh.The invention is illustrated in greater detail below by way of example.
CS 273074 BlCS 273074 Bl
Příklad 1.Example 1.
Teatovania sa uskutečnilo v sklenenom mieSanom reaktora s automatickou raguláciou teploty a odsáváním vznlkojáoobo HgS. Ne tostovnnle ao předložilo 68,4 g PgB^ s obsahom voťnaj síry 1,27 % hmot., 1,7 g elementárnaj síry, čistoty 99,8 % hmot,,The screening was carried out in a glass-stirred reactor with automatic temperature control and suction by HgS. It produced 68.4 g of PgB4 with a free sulfur content of 1.27% by weight, 1.7 g of elemental sulfur, a purity of 99.8% by weight.
45,6 g olejového refinátu. Po vytemperovaní teploty na 40 °C sa postupné přidávala zmes alifatických nasýtenýoh alkoholov tak, aby teplote noprestúpila 100 °C, při ktorej sa reakčná zmes udržiavala počas 2 hodin. Potom sa z reakčnej zmesi odobrale vzorka na analytická kontrolu kyseliny. Zmes sa ochladila na 60 až 80 °C a neutralizovala 27,7 g ZnO v atanola, aby teplota naprestúpila 80 °C. Po ověření pH reakčnej zmesi na indikátor bromfenolovú modrá, sa zmes udržiavala pri teplote 80 - 5 °C počas 1 hodiny. Z takto získanej surověj přísady sa oddeatiloval etanol pri teplota 100 - 105 °C a po přidaní pomocnej filtračnej látky sa filtrovala na vyhrievanom filtri při teplote 80 °C. Rýofalosť filtrácie bola 2 diP h“\lm”2. Filtrát sa odpařil na vákuovej rotačnej odparke za tlaku 2,5 kPa a teploty 90 i 5 °C. Získaná přísada bola číra, bez korozívneho posobenia na Cu plieáok, a vyhovujácim obsahom P, S a Zn. Výťažok dialkyldltiofosforečnanu zinočnatého ne PgS^ bol 96,7 %.45.6 g oil refinate. After warming the temperature to 40 ° C, a mixture of aliphatic saturated alcohols was gradually added so that the temperature did not rise above 100 ° C, maintaining the reaction mixture for 2 hours. A sample was then removed from the reaction mixture for analytical acid control. The mixture was cooled to 60-80 ° C and neutralized with 27.7 g of ZnO in atanol to allow the temperature to rise to 80 ° C. After checking the pH of the reaction mixture for the bromophenol blue indicator, the mixture was maintained at 80-5 ° C for 1 hour. Ethanol was distilled off from the crude additive thus obtained at a temperature of 100-105 ° C and after the addition of the filter aid, it was filtered on a heated filter at 80 ° C. The filtration rate was 2 diP h “lm” 2 . The filtrate was evaporated in a vacuum rotary evaporator at a pressure of 2.5 kPa and a temperature of 90 ° C to 5 ° C. The additive obtained was clear, without corrosive deposition on the Cu plunger, and with satisfactory P, S and Zn contents. The yield of zinc dialkyldiophosphate on PgS4 was 96.7%.
ee
Príkled 2.Example 2.
Postup a podmienky rovnakó ako v příklade 1, ale na reakoiu se nepřidávala síře. Kvalitativně vlastnosti přísady boli rovnakó ako v příklade 1, Změnila sa rýchloať filtráoie na 1 dnP b_* dm’2, t.j. znížila aa o poloviou a výťažok dinlkyldilJoroofbrečnenu zinočnatého na bol 66,3 %. Z porovnanie β příkladem 1 vidiať, ža použitím katalyzátora podťa tohto vynálezu sa zvyáuje výťažok a tiež rýchlosť filtrácie príeady.The procedure and conditions were the same as in Example 1, but sulfur was not added to the reaction. Quality characteristics of ingredients were as for Example 1 has been changed to the rapid filtráoie the DNP 1 b _ * dm 2, and on that is reduced by half, and the yield dinlkyldilJoroofbrečnenu zinc was 66.3%. Comparing β of Example 1, it can be seen that using the catalyst of the present invention increases both the yield and the filtration rate of the case.
Příklad 3.Example 3.
Postup a podmienky rovnakó ako v příklade 1, ale na reakoiu sa navážilo 68,4 g PgS^ s obsahom volnej síry 5,0 % hmot. Rýchlosť filtráoie bola 0,6 dm^hwldm2.The procedure and conditions were the same as in Example 1, but the reaction was weighed with 68.4 g of PgSO4 with a free sulfur content of 5.0 wt. The filtration rate was 0.6 dm 2 h w dm 2 .
Získal sa produkt s vyhovujácim obsahom P, S, Zn s alkalitou, ale bol zakalený a korozívny.A product having a satisfactory P, S, Zn content with alkalinity was obtained, but was cloudy and corrosive.
Příklad 4.Example 4.
Postup a podmienky rovnaké ako v příklade 1, ele na reakoiu sa navážilo 34,2 g PgSg ako v příklade 3 a 34,2 g P2 S5 ako v příklade 1, 0,45 g katalyzátora, síry. Získaný produkt bol číry, bez korozívneho áčinku na Cu plieéok. Z porovnania príkladov 1, 2, 3 a 4 vldieť, že pri zachovaní množstva katalyzátora podlá tohto vynálezu, získá sa přísada s vyhovujácim! kvalitatívnymi vlastnoeťami.Procedure and conditions as in Example 1, but weighing 34.2 g of PgSg as in Example 3 and 34.2 g of P 2 S 5 as in Example 1, 0.45 g of sulfur catalyst, were weighed on the reaction. The product obtained was clear, without corrosive cording on Cu plates. From the comparison of Examples 1, 2, 3 and 4, while maintaining the amount of catalyst according to the present invention, the additive is satisfactorily obtained. qualitative properties.
Příklad 5.Example 5.
Testovanle sa uskutočnilo v prevádzkovej kaskádě miešaných reaktorov. Do prvého člena kaskády sa kontinuálně privádzal PgS^ s obsahom volnej síry 1,1 % hmot., suspendovaný v olejovom rafináte a zmes alifatických nasýtených alkoholov při teplote 100 - 5 °C. V Jaléíob členoch reakčnej kaskády sa uskutočnila neutralizáoio ao suapenziou ZnO v etanole při 85 - 3 °C. Po ťažkostiach pri filtrácii na tanierovom tlakovom filtri a odpaření na vákuovej odparke sa získal produkt s navyhovujácouTesting was carried out in an operating cascade of stirred reactors. The first cascade member was continuously fed with PgS ^ with a free sulfur content of 1.1% by weight, suspended in oil raffinate and a mixture of aliphatic saturated alcohols at 100-5 ° C. Neutralization and suction of ZnO in ethanol at 85-3 ° C were performed in other members of the reaction cascade. After difficulty in filtration on a plate pressure filter and evaporation on a vacuum evaporator, a product with a satisfactory content was obtained.
CS 273074 Bl bazicitou a zakalený. Výťažok produktu na PgS^ bol 91,45 %.CS 273074 B1 basicity and cloudy. The product yield on PgSO4 was 91.45%.
»»
Příklad 6.Example 6.
1'oatup a podmlenky rovnaké ako v příklade 5, ala k 8 °baeboin volhaj uíry1'oatup and conditions as in example 5, ala k 8 ° baeboin volhaj uíry
1,1 % hmot. sa přidával 2,8 % hmot. síry na PgS^. Získal sa produkt Síry, bez problémov pri filtrácii, nekorozívny, s vyhovujúcimi acido-baziokými vlastnoatami. Výťažok produktu na PgS^ bol 95,5 %.1.1 wt. 2.8 wt. of sulfur on PgSO4. A sulfur product was obtained, without filtration problems, non-corrosive, with satisfactory acid-base properties. The product yield on PgS4 was 95.5%.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS321789A CS274074B1 (en) | 1989-05-29 | 1989-05-29 | Method of multi-functional admixture production into lubricating oils on base of zinc dialkyl dithiophosphate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS321789A CS274074B1 (en) | 1989-05-29 | 1989-05-29 | Method of multi-functional admixture production into lubricating oils on base of zinc dialkyl dithiophosphate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS321789A1 CS321789A1 (en) | 1990-08-14 |
| CS274074B1 true CS274074B1 (en) | 1991-04-11 |
Family
ID=5371618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS321789A CS274074B1 (en) | 1989-05-29 | 1989-05-29 | Method of multi-functional admixture production into lubricating oils on base of zinc dialkyl dithiophosphate |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS274074B1 (en) |
-
1989
- 1989-05-29 CS CS321789A patent/CS274074B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS321789A1 (en) | 1990-08-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2809492C2 (en) | Trithio- and tetrathiophosphoric acid triesters, processes for their preparation and for the preparation of trithiophosphorous acid esters and use of the trithio- and tetrathiophosphoric acid triesters | |
| DE60317872T3 (en) | Sulfurized polyisobutylenes wear and oxidation inhibitors | |
| US2723235A (en) | Lubricants | |
| EP0001217A2 (en) | Epithio compounds or mercaptans, and their application in lubricant compositions | |
| US3259579A (en) | Esters of dithiophosphoric acids and lubricating oil compositions containing same | |
| US2378820A (en) | Lubricating oil | |
| DE832030C (en) | Mineral oil based lubricants | |
| DE2647606C2 (en) | ||
| US3396183A (en) | One step preparation of metal organo dithiophosphates | |
| CS274074B1 (en) | Method of multi-functional admixture production into lubricating oils on base of zinc dialkyl dithiophosphate | |
| DE68915760T2 (en) | POLYMER POLYESTERS CONTAINING SULFUR AND ADDITIONAL CONCENTRATES AND LUBRICATING OILS CONTAINING THEM. | |
| JP5044107B2 (en) | Method for reducing crude sediment in metal salts of hydrocarbon dithiophosphoric acid | |
| DE3587624T2 (en) | ADDITIVES FOR LUBRICANTS AND FUNCTIONAL LIQUIDS WHICH HAVE BETTER PERFORMANCE AND METHOD FOR THE PRODUCTION THEREOF. | |
| US4377527A (en) | Ammonia catalyzed preparation of zinc dihydrocarbyl dithiophosphates | |
| DE3872496T2 (en) | SULFURIZED OLEFIN COMPOSITIONS, THEIR PRODUCTION AND THEIR USE AS LUBRICANT ADDITIVES. | |
| DE3855428T2 (en) | Dihydrocarbyl dithiophosphates | |
| US2535024A (en) | Lubricating compositions | |
| US2673881A (en) | Lubricant additives and production thereof | |
| DE69001221T2 (en) | TO POLYALPHAOLEFIN LUBRICANTS, SOLUBLE SULFURIZED OLEFIN POLYMERS. | |
| CN101184828B (en) | Lubricating compositions with improved storage stability | |
| DE2020455C3 (en) | Zinc alkyl thiophosphate mixtures and processes for their preparation and their use | |
| DE69013278T2 (en) | Use of copper and zinc dithiophosphyl dihydrocarbyl dithiophosphate. | |
| US3038013A (en) | Color improvement in synthesis of polysulfides | |
| DE2057167C3 (en) | Detergent additive, a process for its manufacture and its use | |
| US2659705A (en) | Corrosion preventing agent |