DEB0031566MA - - Google Patents
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- DEB0031566MA DEB0031566MA DEB0031566MA DE B0031566M A DEB0031566M A DE B0031566MA DE B0031566M A DEB0031566M A DE B0031566MA
- Authority
- DE
- Germany
- Prior art keywords
- oil
- acids
- soluble
- lubricating oils
- carbon atoms
- 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.)
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- 239000010687 lubricating oil Substances 0.000 claims description 9
- 150000003568 thioethers Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000003460 sulfonic acids Chemical class 0.000 claims description 3
- 125000004432 carbon atoms Chemical group C* 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- -1 alkaline earth metal salts Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- CYQAYERJWZKYML-UHFFFAOYSA-N Phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N Glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N Suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium monoxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HPSUPGAVFFFPMQ-UHFFFAOYSA-N 1,2,3,4,6,7,10-heptachlorododecane Chemical compound CCC(Cl)CCC(Cl)C(Cl)CC(Cl)C(Cl)C(Cl)CCl HPSUPGAVFFFPMQ-UHFFFAOYSA-N 0.000 description 1
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-Dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
- NFIDBGJMFKNGGQ-UHFFFAOYSA-N 2-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=CC=C1O NFIDBGJMFKNGGQ-UHFFFAOYSA-N 0.000 description 1
- QJQIVZBVEBCTKR-UHFFFAOYSA-N 2-(3-methylbutyl)phenol Chemical compound CC(C)CCC1=CC=CC=C1O QJQIVZBVEBCTKR-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- FIWYWGLEPWBBQU-UHFFFAOYSA-N 2-heptylphenol Chemical compound CCCCCCCC1=CC=CC=C1O FIWYWGLEPWBBQU-UHFFFAOYSA-N 0.000 description 1
- MMSQMYOWWBUCMZ-UHFFFAOYSA-N C(CCCCCC)C12C(C=CC=C1)(O)S2 Chemical compound C(CCCCCC)C12C(C=CC=C1)(O)S2 MMSQMYOWWBUCMZ-UHFFFAOYSA-N 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N Isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical class S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 229940036248 Turpentine Drugs 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001553 barium compounds Chemical class 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 230000000994 depressed Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000001050 lubricating Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N propyl 3,4,5-trihydroxybenzoate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
Tag der Anmeldung: 25. Juni 1954 Bekanntgemacht am 8. Dezember 1955Registration date: June 25, 1954. Advertised on December 8, 1955
DEUTSCHES PATENTAMTGERMAN PATENT OFFICE
KLASSE 23c GRUPPE 1oi
B 31566 IVc/23 c CLASS 23c GROUP 1oi
B 31566 IVc / 23 c
sind als Erfinder genannt wordenhave been named as inventors
SchmieröleLubricating oils
Zusatz zum Patent 863 339Addendum to patent 863 339
Gegenstand des Patentes 865 339 sind Schmieröle, die durch einen Gehalt an öllöslichen Zinksalzen von Carbonsäuren mit mindestens 5 Kohlenstoffatomen im Molekül und an öllöslichen Umsetzungsprodukten von Phosphorpentasulfid mit organischen Hydroxylverbindungen gekennzeichnet sind.The subject of patent 865 339 are lubricating oils that contain oil-soluble zinc salts of carboxylic acids with at least 5 carbon atoms in the molecule and of oil-soluble reaction products of phosphorus pentasulphide with organic ones Hydroxyl compounds are labeled.
Gegenstand des Patentes 934 184 sind Schmier-S--öle, die an Stelle der öllöslichen Zinksalze von Carbonsäuren mit mindestens 5 Kohlenstoffatomen im Molekül öllösliche Erdalkalisalze schwefelhaltiger Carbonsäuren mit mindestens 5, zweckmäßig 10 oder mehr Kohlenstoffatomen im Molekül enthalten.The subject of patent 934 184 are lubricating S oils, those in place of the oil-soluble zinc salts of carboxylic acids with at least 5 carbon atoms In the molecule oil-soluble alkaline earth metal salts of sulfur-containing carboxylic acids with at least 5, expedient Contain 10 or more carbon atoms in the molecule.
Gegenstand des Patentes 934 185 sind Schmieröle, die an Stelle der öllöslichen Zinksalze von Carbonsäuren mit mindestens 5 Kohlenstoffatomen im Molekül Ester von schwefelhaltigen Carbonsäuren mit mindestens 5, zweckmäßig 10 oder mehr Kohlenstoffatomen im Molekül enthalten,The subject of the patent 934 185 are lubricating oils that replace the oil-soluble zinc salts of Carboxylic acids with at least 5 carbon atoms in the molecule Esters of sulfur-containing carboxylic acids with at least 5, suitably 10 or more carbon atoms in the molecule,
Gegenstand des Patentes (Patentanmeldung B 31379 IVd/23c) sind Schmieröle, die an Stelle der öllöslichen Umsetzungsprodukte von Phosphorpentasulfid mit organischen Hydroxylverbindungen öllösliche Umsetzungsprodukte von Phosphorpentasulfid mit flüssigen oder festen aliphatischen Kohlenwasserstoffen oder Terpenkohlenwasserstoffen enthalten.The subject of the patent (patent application B 31379 IVd / 23c) are lubricating oils that are an Place of the oil-soluble reaction products of phosphorus pentasulphide with organic hydroxyl compounds Oil-soluble reaction products of phosphorus pentasulphide with liquid or solid aliphatic Contain hydrocarbons or terpene hydrocarbons.
Es wurde gefunden, daß Schmieröle nach Patent 865 339 sowie den Patenten 934 184, 934 185 und (Patentanmeldung B 31379 IVd/23 c),It has been found that lubricating oils according to patent 865 339 and patents 934 184, 934 185 and (patent application B 31379 IVd / 23 c),
509 598/122509 598/122
B 31566 IVc/23 cB 31566 IVc / 23 c
die als weiteren Bestandteil die an sich als Schmierölzusätzc bekannten Alkylphenolsulfide oder deren lister und bzw. oder Sulfonsäuren enthalten, die Bildung kohlenstoffhaltiger Ablagerungen auf den Kolben des Motors in besonders hohem Maße verhindern. as a further component which per se as lubricating oil additional c known alkylphenol sulfides or their lister and / or sulfonic acids containing To the greatest possible extent, prevent the formation of carbonaceous deposits on the pistons of the engine.
Als Alkylphenolsulfide kommen Mono- oder Disulfide in Bet rächt, in denen die Schwefelbrücke gleiche oder verschiedene Alkylphenolreste ver-As alkylphenol sulfides, mono- or disulfides come into consideration, in which the sulfur bridge identical or different alkylphenol radicals
ίο bindet, z. B. Kresol-, Xylenol-, Isobutylphenol-, Isoamylphenol, Ilexylphenol-, Heptylphenol-, Octylplienol-, Dodecylphcnol- und Octodecylphenolreste. Auch Phenole, die mit chlorierten Erdölfraktionen oder chloriertem Paraffin oder mit entsprechendenίο binds, e.g. B. cresol, xylenol, isobutylphenol, Isoamylphenol, Ilexylphenol-, Heptylphenol-, Octylplienol-, Dodecylphenol and octodecylphenol residues. Also phenols made with chlorinated petroleum fractions or chlorinated paraffin or with corresponding
»5 Olefinen alkyliert worden sind, oder solche, die die Alkylreste verzweigter Alkohole aus der Isobutylalkoholsynthese enthalten, können als Grundstoff für die Alkylphenolsulfide dienen. Diese können noch weitere Substituenten enthalten, z. B. Carlxv»5 olefins have been alkylated, or those that have the Alkyl residues of branched alcohols from the isobutyl alcohol synthesis can be used as a base material serve for the alkylphenol sulfides. These can also contain other substituents, e.g. B. Carlxv
so xylgruppcn, funktionell veränderte halogenfreie Carboxylgruppen, wie Ester- oder Amidgruppen, sowie Ätherreste enthaltende Substituenten. Die AlkylphenolsuKide können ganz oder teilweise mit ein oder mehrbasischen Säuren verestert werden.so xyl groups, functionally modified halogen-free Carboxyl groups, such as ester or amide groups, and substituents containing ether groups. the AlkylphenolsuKide can wholly or partially with one or more basic acids are esterified.
Man verwendet hierbei z. B. natürliche Fettsäuren, wie Palmitinsäure oder Stearinsäure, ferner die Fettsäuren, die bei der Oxydation von Paraffin und ähnlichen Kohlenwasserstoffen in der flüssigen Phase entstehen. Auch sind diejenigen Säuren brauchbar, die man durch Oxydation der bei der Umsetzung von Oxyden des Kohlenstoffs mit Wasserstoff gebildeten höheren Alkohole erhält, feiner die Säuren, die durch Einwirkung von Kohlenoxyd und Wasser auf Olefine entstehen, und ferner auch mehrbasische Säuren, wie Oxalsäure, Bernsteinsäure, Glutarsäure, Adipinsäure und Korksäure. Mit Vorteil wird die Veresterung derart durchgeführt, daß noch freie Hydroxylgruppen unverestert bleiben, um in diese Ester noch Metalle, die oben genannt sind, einführen zu können.One uses here z. B. natural fatty acids such as palmitic acid or stearic acid, also the Fatty acids involved in the oxidation of paraffin and similar hydrocarbons in the liquid Phase arise. Also those acids can be used which are obtained by oxidation of the Reaction of oxides of carbon with hydrogen obtained higher alcohols, finer are the acids formed by the action of carbon monoxide and water on olefins, and also polybasic acids such as oxalic acid, succinic acid, glutaric acid, adipic acid and Suberic acid. The esterification is advantageously carried out in such a way that there are still free hydroxyl groups remain unesterified in order to be able to introduce metals, which are mentioned above, into these esters.
Als Sulfonsäuren eignen sich öllösliche Erdöl-Suitable sulfonic acids are oil-soluble petroleum
sulfoiisäurcn, zweckmäßig cyclische Sulfonsäuren mit einer oder mehreren Alkylgruppcn, die 6 bis 15 Kohlenstoffatome in der Alkylgruppe enthalten, insbesondere ihre Salze. .sulfoic acids, expediently cyclic sulfonic acids with one or more alkyl groups containing 6 to 15 carbon atoms in the alkyl group, especially their salts. .
Die Mischung der Komponenten wird in der Weise vorgenommen, daß man etwa 40 bis 70% öllösliche Erdalkalisalze schwefelhaltiger Carbonsäuren oder deren Ester, io'bis 20% der Umsetzungsprodukte von Phosphorsulfiden mit Kohlen-Wasserstoffen und 10 bis 40% Alkylphenolsulfid verwendet. Dieses Gemisch wird einem Schmieröl in einer Menge von 0,1 bis 10% zugegeben. Gleichzeitig kann man noch Schaumverhinderungsmittcl, Stockpunktserniedriger und Viskositätsverbesserer zusetzen.The components are mixed in such a way that about 40 to 70% Oil-soluble alkaline earth salts of sulfur-containing carboxylic acids or their esters, 10% to 20% of the reaction products of phosphorus sulfides with hydrocarbons and 10 to 40% alkylphenol sulfide used. This mixture is added to a lubricating oil in an amount of 0.1 to 10%. Simultaneously You can also use foam inhibitors, pour point depressants and viscosity improvers to add.
130 Teile Propylester einer Spermölfettsäure, die mit gemahlenem Schwefel bei etwa 2000 behandelt und mit Bleicherde raffiniert wurde, 60 Teile der Bariumverbindung von Heptylphenolsulfid und 60 Teile eines öllöslichen Zink-Calcium-Salzes einer Dodecylbenzolsulfonsätire werden in 670 Teilen Motorenöl bei ioo° gelöst. Dann gibt man 180Teile eines Bariumsalzes aus einem Umsetzungsprodukt von Terpentinöl mit Phosphorpentasulfid zu, das bei 50 bis 1300 hergestellt wurde. Dieses Produkt wird mit geringen Mengen gebranntem Kalk, Wasser und Methanol bei 80 bis 1300 behandelt und dabei leicht alkalisch gemacht.130 parts of propyl ester of a sperm oil, which was treated with ground sulfur at approximately 200 0 refined with bleaching earth, 60 parts of the barium compound of Heptylphenolsulfid and 60 parts of an oil-soluble zinc-calcium salt of a Dodecylbenzolsulfonsätire are dissolved in 670 parts of motor oil at ioo °. Are then added to 180Teile a barium salt of a reaction product of turpentine with phosphorus pentasulfide, which was prepared at 50 to 130 0th This product is treated with small amounts of quick lime, water and methanol at 80 to 130 0 thereby made slightly alkaline.
Nach dem Zentrifugieren erhält man ein Schniierölverbesserungsmittel mit ausgezeichneten Detergent- und Inhibitoreigenschaften.A cutting oil improver is obtained after centrifugation with excellent detergent and inhibitor properties.
Claims (1)
Family
ID=
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