US3655559A - Alkylated diphenylamines as stabilizers - Google Patents

Alkylated diphenylamines as stabilizers Download PDF

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Publication number
US3655559A
US3655559A US27176A US3655559DA US3655559A US 3655559 A US3655559 A US 3655559A US 27176 A US27176 A US 27176A US 3655559D A US3655559D A US 3655559DA US 3655559 A US3655559 A US 3655559A
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compound
percent
diphenylamine
weight
parts
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Brian Holt
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Novartis Corp
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Ciba Geigy Corp
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    • 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
    • C10N2010/08—Groups 4 or 14
    • 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
    • C10N2010/10—Groups 5 or 15
    • 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—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • eight carbon atoms and may be, for instance a tertiary-butyl
  • tertiary-.pentyl (lzl-dimethylpropyl), tertiary-hexyl (1:1- dimethylbutyl), tertiary-octyl (121:3:3-tetramethylbutyl) or a nonyl or dodecyl group, derived from propylene trimer or tetramer respectively which are commercially-available mixtures of isomeric nonenes or dodecenes.
  • the substituents R and R may be, for example, an ethyl, isopropyl or a tertiarybutyl group.
  • Examples of'preferred used compounds of formula I include 2:2-diethyl-4:4-di-t-butyl-diphenylamine, 2:2-diethyl-4:4'- di-tsoctyl-diphenylamine, 2:4:4'-tri-t-butyhdiphenylamine and particularly 2:23:424BQ-tetra-t-butyldiphenylamine.
  • the compounds having the formula I are produced by ortboalkylating in a first stage, diphenylamine with a straightor branched-chain olefine having from two to four carbon atoms per; molecule in the presence of a catalyst comprising aluminum, and in a second stage, contacting the thus orthoalkylated diphenylamine with a secondary olefme having from four to- L2 carbon atoms per molecule, in the presence. of a. Friedel-Crafts or Bronsted acid catalyst.-
  • the compounds of formula I are thus. conveniently produced for instance, by first alkylating diphenylamine in one or both of the ortho- (2 and 2' positions) of the diphenylamine molecule, and subsequently alkylatin'g the orthoalkylatedgmaterial in both of the para: (.4 and.4') positions.
  • the proportion, of olefine to that of diphenylamine. in the orthoralkylation reactionmixture isdesirably substantially.
  • the proportion. of olefine todiphenylamine isdesirably within the range of from lt. 0;to l 1 moles per moleof diphenylamine.
  • the proportion of olefineto diphenylamine is advantageously within-the, range of from 2,0 to 2.5 moles of" olefine per molecule of dipheny m ne
  • Thecatalystused in theorthoalkylation step may be, for example, aluminum metal; itself;,aluminum amalgam alone or in combination with an alloy. for instance,,aluminum.and. nickel; oraluminum or aluminumamalgam in combinationwith mercury. salts for instance, mercuric chloride.
  • a preferred form of catalyst is aluminum metalor acompound of aluminum, with diphenylaminecontaining a; FriedelsCrafts catalystzor Fullers earth, especially mixtures of. aluminum metal with.
  • step consists of a mixture of aluminum chloride with an alkali metal, especially sodium metal which provides a particularly active form of orthoalkylation catalyst probably consisting of aluminum metal in combination with aluminum chloride.
  • Normal catalytic amounts of the catalyst are desirably employed in the orthoalkylation process, for example, an amount of catalyst within the range of from 0.1 percent to 10 percent by weight based on the weight of diphenylamine starting material.
  • the total content of aluminum in the catalyst, where a mixed catalyst is used, may vary widely but is preferably within the range of from 10 percent to percent by weight based on the total weight of the catalyst.
  • the orthoalkylation reaction may be carried out at substantially atmospheric pressure but is advantageously effected at superatmospheric pressure and at an elevated temperature.
  • the reaction is preferably conducted in a pressure reactor, optionally equipped with an agitating device.
  • the reaction temperature may be, for example, within the range of from to 400 C.
  • the orthoalkylation step is effected by reacting the diphenylamine and the gaseous olefine reactant in a sealed reactor at a superatmospheric pressure within the range of from 2 to 400 atmospheres.
  • the progress of the reaction may be followed by observing the degree of the drop in pressure as the gaseous olefine is consumed.
  • the desired 2- and/or 2:2'-di-ortho-alkylated diphenylamine may be separated from the reaction mixture by conventional techniques, for example by fractional distillation under reduced pressure.
  • the orthoalkylated compound is further alkylated by contacting said orthoalkylated diphenylamine with the secondary olefine having from four to 12 carbon atoms per molecule in the presence of a Friedel-Crafts or Bronsted acid catalyst, and preferably at atmospheric pressure. It is particularly preferred to use a Friedel-Crafts catalyst in the further aklylation step.
  • Suitable Friedel-Qrafts catalysts include ferric chloride, stannic chloride, zinc chloride, boron trifuloride and diethyl ether complexes thereof, titanium tetrachloride and, preferably, aluminum chloride especially in a substantially anhydrous form.
  • Secondary olefines include iso-butylene, 2-methyl pentene-l diisobutylene and propylene trimer.
  • a Bronsted acid catalyst may be, for example, sulphuric acid, phosphoric acid, an organic sulphonic acid, adialkyl sulphate or a mixture of two or more thereof.
  • lfsulphuric acid is present as a catalyst, it may be for'example, in. the form of concentrated sulphuric acid, oleum or an aqueous solution of the acid, but is preferably sulphuric acid monohydrate,.namely an. equimolar mixture of concentrated sulphuric acid (H 50 and water.
  • phosphoric acid is present as catalyst, it may be, for example, in. the form of orthophosphoric acid or an aqueous solution of the orthophosphoric acid,.for instance a' substantially equimolar mixture of 'orthophosphoric acid (HgPOQand water.
  • Friedeli-Crafts or Bronstedacid'catalyst whichzis employed in the process of the present invention is conveniently within the range of from 0.01 to L5 moles of catalyst per mole of orthoalkylated diphenylamine compound, a proportion of Friedel-Crafts or Bronsted acid catalyst within. the range. of from: 0.1. to 0.5 mole of catalyst per mole of orthoalkylated diphenylamine compound being especially preferred.
  • the para-alklylation step is advantageously carried out in the absenceaof. an'added inert solvent.
  • the olefine is a liquid.
  • olefine such as diisobutylene
  • the para-alkylation step is conveniently effectedby charging the reactants into a reactor and using-iexcess liquid olefine as thereaction solvent.
  • the reaction mixture is desirablycharged into a reactor and the gaseous olefine blown through'the molten orthoalkylated diphenylamine starting. material containing the Bronsted acid or Friedel-Crafts catalyst.
  • the rate at which the gaseous olefine is blown through the reaction melt is advantageously within the range of from 50 milliliters to 300 milliliters per minute, per mole of o-alkylated diphenylamine.
  • the reaction temperature is preferably within the range of from 80 to 200 C. If, however, the para-alkylation reaction step is efiected using a gaseous olefine the reaction temperature is preferably the minimum temperature which is sufficient to maintain a reaction melt through out the reaction period. In the latter case, normally and preferably the temperature of the reaction melt is within the range of from 100 to 200 C. and the reaction is also preferably conducted in an inert atmosphere, for instance a nitrogen atmosphere.
  • the para-alkylation step is preferably concluded in the presence of a substantial excess of the secondary olefine reactant over the stoichiometric proportion required.
  • the proportion of secondary olefine is preferably within the range of from 2.0 to 3.0 moles per mole of orthoalkylated diphenylamine.
  • the desired triand/or tetra-alkylated diphenylamine may be isolated from the final reaction mixture by any conventional technique.
  • the final reaction mixture may be dissolved in an organic solvent, such as toluene or xylene and washed with aqueous sodium hydroxide and then with water, to neutrality. Removal of the organic solvent then provides the crude reaction product which may be further purified, if desired, by distillation, for instance under reduced pressure and/or by recrystallisation from a suitable solvent such as ethanol.
  • R is hydrogen or a teriary-butyl group
  • R can be also produced by contacting in a single stage diphenylamine with iso-butylene in the presence of a Friedel-Crafts or Bronsted acid catalyst.
  • the process of producing a compound of formula II is conveniently effected by charging the diphenylamine starting material and the F riedel-Crafts or Bronsted acid catalyst into a reactor and heating the mixture to a temperature above its melting point, for instance to a temperature within the range of from 60 to 200 C. more preferably within the range of from lto 200 C., and passing the iso-butylene through the reaction melt.
  • the rate at which the iso-butylene is passed through the melt is desirably within the range of from 50 milliliters to 300 milliliters per minute.
  • the process is conducted in an inert atmosphere, especially in an atmosphere of nitrogen.
  • the iso-butylene gas is advantageously passed through the molten reaction mixture until the iso-butylene ceases to be absorbed by the melt.
  • the time required to achieve the maximum absorption of isobutylene at the preferred rate of passage through the melt, defined hereinbefore, is normally within the range of from 2 to 10 hours. If, however, it is desired to produce predominantly 2:224-tri-tbutyl dipehnylamine, the passage of iso-butylene is desirably terminated when substantially three molecules of iso-butylene have been absorbed per mole of diphenylamine starting material.
  • the desired trior tetra-tbutyl diphenylamine may be separated from the other components of the reaction mixture by conventional methods.
  • the crude reaction mixture may be dissolved in an 4 organic solvent such as toluene or xylene, washed with aqueous alkali, especially aqueous sodium hydroxide, and water to neutrality, and subsequently fractionally distilling the washed residue.
  • the product so obtained may be further purified, if desired, by fractional crystallization from an organic solvent, particularly methanol or ethanol.
  • reaction may be effected at an elevated pressure if desired, it is preferred that the reaction is conducted at substantially atmospheric pressure in order to avoid the use of expensive pressure equipment.
  • the Friedel-Crafts or Bronsted catalyst employed in the process of producing the compound of Formula ll may be any of the catalysts within the groups specified hereinbefore. However, it is particularly preferred to use aluminum chloride in any fonn of this catalyst which possesses a high degree of activity in promoting Friedel-Crafts alkylation processes.
  • a particularly preferred form of the catalyst consists of the freshlyprepared, substantially anhydrous material. The catalyst is desirably employed in conventional catalytic amounts, for example in a proportion within the range of from 0.1 percent to 10 percent by weight based on the total weight of the diphenylamine starting material.
  • compositions obtained by the present invention preferably contain a proportion of antioxidant of the present invention within the range of from 1.001 percent to 5.0 percent by weight based on the weight of the organic material. More preferably, the compositions contain a proportion of antioxidant within the range of from 0.1 percent to 4.0 percent by weight based on the weight of the organic material.
  • the amount of antioxidant employed in any particular organic material will depend not only on the nature of the organic material but also on the external conditions under which the material is to be used. Thus organic materials to be used at normal temperatures will usually require a smaller proportion of antioxidant than organic materials, such as synthetic lubricants, designed for use at elevated temperatures.
  • a particular class of organic material susceptible to oxidative deterioration for which the compounds used according to the present invention are particularly valuable as antioxidants is that consisting of synthetic lubricants, especially those derived from carboxylic esters and intended for use at temperatures at or above 400 F.
  • esters examples include lubricants based on a diester of a dibasic acid and a monohydric alcohol, for instance dioctyl sebacate or dinonyl adipate; on a triester of 1:111- trimethylol propane and a monobasic acid or mixture of such acids, for instance 1:1:l-trimethylol propane tripelargonate, 1:1:1-tn'methylol propane tricaprylate or mixtures thereof; on a tetraester of pentaerythritol and a monobasic acid or mixture of such acids, for instance pentaerythritol tetracaprylate; or on complex esters derived from lzlzl-trimethylol propane, caprylic acid and sebacic acid; or on mixtures thereof.
  • the synthetic lubricant may also contain other additives such as further antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour-point depressants, dispersants or detergents, extreme pressure or antiwear additives, antifoams, antiknock additives and antiicing additives or carburetor detergents.
  • additives such as further antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour-point depressants, dispersants or detergents, extreme pressure or antiwear additives, antifoams, antiknock additives and antiicing additives or carburetor detergents.
  • Suitable examples of further antioxidants include those contained in the following groups (a) to (h):
  • Alkylated and non-alkylated aromatic amines and mixtures thereof for example dioctyldiphenylamine; mono-t-octylphenyl-a and B-naphthylamines; dioctylphenothiazine; Phenyl-a-naphthylamine;
  • Hindered phenols for example 2,6di tertiarybutyl-pcresol; 4,4-bis-( 2,6-diisopropylphenol); 2,4,6- triisopropylphenol; 2,2 thio-bis-( 4-methyl-6-tert-butylphenol)
  • Alkyl, aryl or alkaryl phosphites for example, triphenylphosphite; trinonylphosphite; diphenyldecylphosphite;
  • esters of thiodipropionic acid for example, dilaurylthiodipropionate
  • Salts of carbamic and dithiophosphoric acids for example, antimony diamyldithiocarbamate, zinc diamyldithiophosphate;
  • Metal salts complexes of organic cholating agents for example, copper bis (trifluoroacetylacetonates), copper phthalocyanines, tributyl ester of EDTA, monosodium salt;
  • Free radical antioxidants and their precursors for example, amine oxides and nitroxides
  • antioxidants from any of the above sections, for example, an alkylated amine and a hindered phenol.
  • suitable metal passivators include those of the following types:
  • a. for copper for example, benzotriazole, 5,5-methylenebisbenzotriazole, tetrahydrobenzotriazole, 2,5-dimercaptothiadiazole, salicylidene-propylenediamine, salts of salicylalaminoguanidine; and quinizarin;
  • magnesium for example, propyl gallate
  • c. for lead for example, sebacic acid.
  • Rust inhibitors which may be employed in the lubricant compositions include those of the following groups:
  • Organic acids, and their esters, metal salts, anhydrides for example, N-oleoyl sarcosine, sorbitan mono-oleate, lead naphthenate and dodecenylsuccinic anhydride.
  • Nitrogen-containing materials for example,
  • heterocyclic compounds for example, imidazolines, and
  • Phosphorous-containing materials for example, inorganic phosphates, phosphonic acids and amine phosphates.
  • Sulphur-containing materials for example, barium dinonylnaphthalene sulphonates.
  • Suitable viscosity index improvers or pour-point depressants are, for instance, polyacrylates, polybutenes and polyvinyl pyrrolidones.
  • dispersant or detergents examples include metal sulphonates especially calcium, barium and magnesium salts, metal phenates and polybutenyl succinimides.
  • Extreme pressure or antiwear additives appropriate for use in the lubricant composition include sulphur and/or phosphorus and/or halogen containing materials, for instance, sulphurized sperm oil, tritolyl phosphate and chlorinated paraffins.
  • Siliconcs are particularly suitable as antifoams and lead alkyls are eminently suitable as antiknock additives for the lubricant compositions of the invention.
  • antiicing additives or carburetor detergents include, for instance, glycol ethers, imidazolines and amine phosphates.
  • antioxidants include, for instance, substances falling within the following groups: p
  • a. materials consisting of, or based on, aliphatic or other hydrocarbons, for instance, gasoline, lubricating oils, lubricating greases, mineral oils and waxes.
  • natural and synthetic polymeric materials for instance, natural rubber
  • synthetic addition polymers such as homopolymers and co-polymers of vinyl and vinylidene monomers including ethylene, propylene, styrene, butadiene, acrylonitrile, vinyl chloride or vinyl acetate
  • non-polymeric oxygen-containing substances for in stance, aldehydes such as n-heptaldehyde, and unsaturated fatty acids or esters thereof, for instance, methyl oleate and ricinolcic acid.
  • organo-metalloid substances such as silicone polymers. for instance, polydimethylsiloxanes, polymethylphenylsiloxanes and chlorinated derivatives thereof; silanes, for instance, tetra-alkyl and tetra-aryl silanes; and organo-metallic substances such as organo-metallic polymers.
  • the compounds of Formula I may be employed in multi-ingredient compositions, that is compositions containing at least one organic substance susceptible to oxidative deterioration or a mixture thereof and one or more organic or inorganic compounds, for instance, an alcoholic or aqueous emulsion of an organic material susceptible to oxidative deterioration.
  • EXAMPLE 1 69 Parts of 2:2'-diethyldiphenylamine and 0.7 part of anhydrous aluminum chloride were charged into a reactor and the mixture heated to 130 C., cooled to 100 C. At this tem perature 85.9 parts of diisobutylene were added to the mixture over a period of 2 hours and the mixture was then heated under reflux conditions until the temperature of the reflux mixture reached 160 C. After cooling, the reaction mixture was taken up in 500 parts of toluene and washed with aqueous 10 percent sodium hydroxide and then with water to neutrality. Removal of the toluene solvent under vacuum furnished 110.7 parts of a crude product as an oil. This oil was distilled to give a product which solidified on cooling. Recrystallization of this solid from ethanol gave 2:2'-diethyl-4:4'-di-t-octyl diphenylamine having melting point of 63 C. and having the following elemental analysis by weight:
  • EXAMPLE 2 169 Parts of diphenylamine and 4.4 parts of anhydrous aluminum chloride were charged into a reactor and the mixture heated to a temperature of 140 C. under an atmosphere of nitrogen to give a liquid melt. Isobutylene was then passed through the melt at a rate of 200 milliliters per minute until absorption of isobutylene ceased, after a period of 5.5 hours.
  • EXAMPLES 3-5 A synthetic ester-based lubricant was formulated and subjected to the Pratt and Whitney Type 11 oxidation-corrosion test.
  • the base fluid was a complex ester derived from sebacic acid, caprylic acid and trimethylol propane, the complex ester being described and claimed in British Pat. No. 971,901.
  • Each test was carried out for 48 hours at a temperature of 425 C. using dry air at a rate of 5 liters per hour and in the presence of specimens of magnesium alloy, aluminum alloy, copper, silver and steel.
  • Table I illustrate well the excellent properties of the lubricant compositions of the present invention 2.
  • EXAMPLE 75.12 Parts by weight of 2,2'-di-ethyldiphenyla.mine and 1.5 parts by weight of anhydrous aluminum chloride were charged into a reactor and the mixture heated to a temperature of 140 C. under an atmosphere of nitrogen to give a liquid melt. lsobutylene was then passed through the melt at a rate of 200 milliliters per minute until absorption of isobutylene ceased, after a period of 3 hours. After cooling, the reaction mixture was taken up in 300 parts by weight of toluene and washed with aqueous percent sodium hydroxide and then with water to neutrality.
  • EXAMPLE 9 169 parts by weight of diphenylamine and 4.4 parts by weight of anhydrous aluminum chloride were charged into a reactor and the mixture heated to a temperature of 140 C. under an atmosphere of nitrogen to give a liquid melt. The reaction mixture was then cooled to 100 C. and 336 parts by weight of diisobutylene were added over a period of 15 minutes, the reaction mixture was then refluxed for a further 48 hours. After cooling, the reaction mixture was taken up in 500 parts of toluene and washed with aqueous 10 percent sodium hydroxide and then with water to neutrality. Removal of the toluene solvent under vacuum fumished 400 parts of a crude product as an oily solid.
  • EXAMPLE 1 l 9.9 parts of 2,2-di-isopropyldiphenylamine and 0.16 parts of anhydrous aluminum chloride were charged into a reactor and the mixture heated to a temperature of C. under an atmosphere of nitrogen to give a liquid melt. lsobutylene was then passed through the melt at a rate of 200 milliliters per minute until absorption of isobutylene ceased, after a period of 5 hours. After cooling, the reaction mixture was taken up in 100 parts of toluene and washed with aqueous sodium hydroxide and then with water to neutrality. Removal of toluene solvent under vacuum furnished 12.8 parts of a pink oil which slowly solidified.
  • Samples of the respective dry powders were then placed in a I claim: mould (6.0 inches X 6.0 inches X 0.015 inch).
  • the mould was 1.
  • a method of stabilizing synthetic carboxylic acid ester then heated in a press under constant pressure for 5 minutes.
  • lubricating oils which comprises incorporating in said A pressure of 20 tons/square inch was applied for 1 minute, synthetic carboxylic acid ester lubricating oils a compound cooling was commenced and pressure increased so that when 5 having the formula: the temperature reached 150 C., the pressure was 80 tons/square inch. Cooling was continued to 50 C., when the mould was removed from the press.
  • the results achieved, including a control experiment, are 15 y g or a Stralght branched chain alkyl group set out below: 15 having from two to four carbon atoms, and
  • R' is a straight or branched chain alkyl group having from Time to two to four carbon atoms.
  • R has from four to eight no add g carbon atoms in the alkyl chain. g5if flfg flifliigig iggg ii$gfigfigigfig "7' 3.
  • R is a tertiary butyl, tertia- 22 -d s p W i-t-butyldiphe yl m 16 ry pentyl, tertiary hexyl, tertiary octyl or a nonyl group derived from propylene trimer. 4.
  • R" and R are ethyl, EXAMPLES 15-17 isopropyl or tertiary butyl. The following synthetic rubber formulation was made up: 25 5.
  • a method of claim 1 wherein said compound is 2:2-
  • stearic acid 2 items 7 A method of claim 1 wherein said compound is 2:2:4-triii i i 2:2: t-butyldiphenylamine.
  • a composition comprising a synthetic carboxylic acid
  • the formulations were Pl' p a two'rou accord ester lubricating oil susceptible to oxidative deterioration and, mg to the @"t Sequential procedure: as an antioxidant, a compound of claim 1.
  • a composition as claimed in claim 10 wherein the proi i of zmc Oxide Steam acid f antloxldam' portion of the compound of claim 1 is within the range of from i i of P 9 the day after 5 mmutes- 40 0.001 percent to 5 percent by weight based on the weight of Addlllon 0f remamdef 0f the y after 15 mmmesthe synthetic carboxylic acid ester lubricating oil. Addition of accelerators after 20 mmutes- 12.
  • a composition as claimed in claim 10 wherein the pro- Addition of Sulphur, cutting rollillg after 25 mmutesportion of the compound of claim 1 is within the range of from Grinding, Six Passes through a tight P- 0.1 percent to 4.0 percent by weight based on the weight of
  • the optimum cure times for the various samples were then h Synthetic b li id ester l b i i] determined using the R.A.P.R.A. (Rubber and Plastics 13, A iti as l i d i l i 10 h i h Research Association) Cu o e e
  • the s p were then synthetic carboxylic acid ester lubricating oil is intended for vulcanized at 153 C.
  • Table IV also conmonobasic acid or mixture of such esters; or on complex tains details relating toacontrol experiment. esters derived from l:lzl-trimethylolpropane, caprylic acid 7 V and sebacic acid; or on mixtures thereof.

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US27176A 1969-04-11 1970-04-09 Alkylated diphenylamines as stabilizers Expired - Lifetime US3655559A (en)

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Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3979180A (en) * 1975-09-12 1976-09-07 National Distillers And Chemical Corporation Stabilized crosslinked polyethylene and ethylene-vinyl acetate
US4186105A (en) * 1976-07-21 1980-01-29 Imperial Chemical Industries Limited Antioxidants
US4298481A (en) * 1979-02-23 1981-11-03 Tenneco Chemicals, Inc. High temperature grease compositions
US4440671A (en) * 1982-03-31 1984-04-03 Union Carbide Corporation Compositions of hydrocarbon-substituted diphenyl amines and high molecular weight polyethylene glycols; and the use thereof as water-tree retardants for polymers
US4704219A (en) * 1985-07-05 1987-11-03 The B. F. Goodrich Company Novel composition of para-butylated and octylated, ortho-ethylated diphenylamines
US4739121A (en) * 1984-05-24 1988-04-19 The B. F. Goodrich Company Process for otho- and para-alkylating diphenylamines
US4797511A (en) * 1987-09-25 1989-01-10 Uniroyal Chemical Company, Inc. Polyethylene stabilized by mixture of hindered phenol and amine antioxidants
US4837259A (en) * 1987-09-25 1989-06-06 Uniroyal Chemical Company, Inc. Polypropylene stabilized against oxidative degradation with mixtures of diarylamine derivatives and sterically hindered phenols
US4925889A (en) * 1987-09-25 1990-05-15 Uniroyal Chemical Company, Inc. Stabilized carbon black loaded polyolefins
US5180514A (en) * 1985-06-17 1993-01-19 The Clorox Company Stabilizing system for liquid hydrogen peroxide compositions
US5321159A (en) * 1992-12-18 1994-06-14 The B. F. Goodrich Company Decolorization of alkylated diarylamines
US5373028A (en) * 1991-08-20 1994-12-13 The Dow Chemical Company Polyurethane foams having reduced visible emissions during curing
US5489711A (en) * 1994-12-20 1996-02-06 The B. F. Goodrich Company Synthetic lubricant antioxidant from monosubstituted diphenylamines
US5503760A (en) * 1992-05-02 1996-04-02 Henkel Kommanditgesellschaft Auf Aktien Engine base oils with improved seal compatibility
US5520848A (en) * 1990-09-13 1996-05-28 Ciba-Geigy Corporation Mixtures and compositions containing phenothiazines
US5571453A (en) * 1994-10-25 1996-11-05 Uniroyal Chemical Company, Inc. Stabilized polyether polyol and polyurethane foam obtained therefrom
US5607907A (en) * 1993-10-15 1997-03-04 Oronite Japan Limited Multipurpose functional fluid for agricultural machinery or construction machinery
US5672752A (en) * 1995-09-13 1997-09-30 The Bfgoodrich Company Liquid alkylated diphenylamine antioxidant
US5750787A (en) * 1995-09-13 1998-05-12 B. F. Goodrich Company Liquid alkylated diphenylamine antioxidant
US5834544A (en) * 1997-10-20 1998-11-10 Uniroyal Chemical Company, Inc. Organic materials stabilized by compounds containing both amine and hindered phenol functional functionalities
US6204412B1 (en) 1999-04-16 2001-03-20 The B. F. Goodrich Company Method of manufacturing alkylated diphenylamine compositions and products thereof
US6426324B1 (en) 1993-12-15 2002-07-30 Noveon Ip Holdings Corp. Lubricant composition
US6573224B2 (en) * 1997-01-03 2003-06-03 Bardahl Manufacturing Corporation Two-cycle engine lubricant composition comprising an ester copolymer and a diester
US20070142243A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Synergistic lubricating oil composition containing a mixture of a benzo[b]perhydroheterocyclic arylamine and a diarylamine
US20070142245A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions
US20070142246A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions
US20080202660A1 (en) * 2006-12-21 2008-08-28 Abdallah David G Rubber Composition and Pneumatic Tire Using Same
US20080318815A1 (en) * 2007-06-20 2008-12-25 Chevron Oronite Company Llc Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a dairylamine
EP2077315A1 (fr) 2007-12-20 2009-07-08 Chevron Oronite Company LLC Compositions d'huile de lubrification contenant un antioxydant de diamine Tetraalkyl-Napthalène-1,8
US20100152079A1 (en) * 2007-12-20 2010-06-17 Chevron Oronite Company Llc Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant
US20110124538A1 (en) * 2008-08-08 2011-05-26 Albemarle Corporation Octylated Phenyl-Alpha-Naphthylamine Product Mixtures And Production Of Such Mixtures Having A High Content Of Octylated Phenyl-Alpha-Naphthylamine
US20160152789A1 (en) * 2013-07-11 2016-06-02 Nok Corporation Nitrile rubber composition
WO2016123717A1 (fr) * 2015-02-06 2016-08-11 University Of Ottawa Antioxydants et procédés pour maximiser les performances
WO2022108298A1 (fr) * 2020-11-17 2022-05-27 Songwon Industrial Co., Ltd. Compositions comprenant des diphénylamines alkylées présentant des propriétés améliorées
US12168726B2 (en) 2018-11-30 2024-12-17 Si Group, Inc. Antioxidant compositions
US12486467B2 (en) 2021-06-25 2025-12-02 Songwon Industrial Co., Ltd. O-alkylated sterically hindered antioxidants

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0097118A3 (fr) * 1982-06-10 1984-07-25 Ciba-Geigy Ag Liquides antioxydants pour lubrifiants et élastomères
US4414348A (en) * 1983-01-26 1983-11-08 The Goodyear Tire & Rubber Company Stabilized polyester compositions
EP0407124A1 (fr) * 1989-07-07 1991-01-09 Tonen Corporation Composition d'huile lubrifiante
GB2294696A (en) * 1994-11-04 1996-05-08 Exxon Research Engineering Co Marine lubricant composition

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2009480A (en) * 1932-06-10 1935-07-30 Goodrich Co B F Antioxidant
US3052632A (en) * 1959-02-11 1962-09-04 Shell Oil Co High temperature grease compositions
US3282840A (en) * 1962-11-29 1966-11-01 Eastman Kodak Co Stable lubricating composition and inhibitor mixture therefor

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2009480A (en) * 1932-06-10 1935-07-30 Goodrich Co B F Antioxidant
US3052632A (en) * 1959-02-11 1962-09-04 Shell Oil Co High temperature grease compositions
US3282840A (en) * 1962-11-29 1966-11-01 Eastman Kodak Co Stable lubricating composition and inhibitor mixture therefor

Cited By (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3979180A (en) * 1975-09-12 1976-09-07 National Distillers And Chemical Corporation Stabilized crosslinked polyethylene and ethylene-vinyl acetate
US4186105A (en) * 1976-07-21 1980-01-29 Imperial Chemical Industries Limited Antioxidants
US4298481A (en) * 1979-02-23 1981-11-03 Tenneco Chemicals, Inc. High temperature grease compositions
US4440671A (en) * 1982-03-31 1984-04-03 Union Carbide Corporation Compositions of hydrocarbon-substituted diphenyl amines and high molecular weight polyethylene glycols; and the use thereof as water-tree retardants for polymers
US4739121A (en) * 1984-05-24 1988-04-19 The B. F. Goodrich Company Process for otho- and para-alkylating diphenylamines
US5180514A (en) * 1985-06-17 1993-01-19 The Clorox Company Stabilizing system for liquid hydrogen peroxide compositions
US4704219A (en) * 1985-07-05 1987-11-03 The B. F. Goodrich Company Novel composition of para-butylated and octylated, ortho-ethylated diphenylamines
US4797511A (en) * 1987-09-25 1989-01-10 Uniroyal Chemical Company, Inc. Polyethylene stabilized by mixture of hindered phenol and amine antioxidants
US4837259A (en) * 1987-09-25 1989-06-06 Uniroyal Chemical Company, Inc. Polypropylene stabilized against oxidative degradation with mixtures of diarylamine derivatives and sterically hindered phenols
US4925889A (en) * 1987-09-25 1990-05-15 Uniroyal Chemical Company, Inc. Stabilized carbon black loaded polyolefins
US5520848A (en) * 1990-09-13 1996-05-28 Ciba-Geigy Corporation Mixtures and compositions containing phenothiazines
US5373028A (en) * 1991-08-20 1994-12-13 The Dow Chemical Company Polyurethane foams having reduced visible emissions during curing
US5503760A (en) * 1992-05-02 1996-04-02 Henkel Kommanditgesellschaft Auf Aktien Engine base oils with improved seal compatibility
US5321159A (en) * 1992-12-18 1994-06-14 The B. F. Goodrich Company Decolorization of alkylated diarylamines
US5607907A (en) * 1993-10-15 1997-03-04 Oronite Japan Limited Multipurpose functional fluid for agricultural machinery or construction machinery
US6426324B1 (en) 1993-12-15 2002-07-30 Noveon Ip Holdings Corp. Lubricant composition
US5571453A (en) * 1994-10-25 1996-11-05 Uniroyal Chemical Company, Inc. Stabilized polyether polyol and polyurethane foam obtained therefrom
US5489711A (en) * 1994-12-20 1996-02-06 The B. F. Goodrich Company Synthetic lubricant antioxidant from monosubstituted diphenylamines
US5672752A (en) * 1995-09-13 1997-09-30 The Bfgoodrich Company Liquid alkylated diphenylamine antioxidant
US5750787A (en) * 1995-09-13 1998-05-12 B. F. Goodrich Company Liquid alkylated diphenylamine antioxidant
US6573224B2 (en) * 1997-01-03 2003-06-03 Bardahl Manufacturing Corporation Two-cycle engine lubricant composition comprising an ester copolymer and a diester
US5834544A (en) * 1997-10-20 1998-11-10 Uniroyal Chemical Company, Inc. Organic materials stabilized by compounds containing both amine and hindered phenol functional functionalities
US6204412B1 (en) 1999-04-16 2001-03-20 The B. F. Goodrich Company Method of manufacturing alkylated diphenylamine compositions and products thereof
US20070142245A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions
US8003583B2 (en) 2005-12-21 2011-08-23 Chevron Oronite Company Llc Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions
US20070142246A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions
US7285518B2 (en) 2005-12-21 2007-10-23 Chevron Oronite Company Llc Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions
US7501386B2 (en) 2005-12-21 2009-03-10 Chevron Oronite Company, Llc Synergistic lubricating oil composition containing a mixture of a benzo[b]perhydroheterocyclic arylamine and a diarylamine
US20070142243A1 (en) * 2005-12-21 2007-06-21 Chevron Oronite Company Llc Synergistic lubricating oil composition containing a mixture of a benzo[b]perhydroheterocyclic arylamine and a diarylamine
US20080202660A1 (en) * 2006-12-21 2008-08-28 Abdallah David G Rubber Composition and Pneumatic Tire Using Same
US8939184B2 (en) 2006-12-21 2015-01-27 Bridgestone Americas Tire Operations, Llc Rubber composition and pneumatic tire using same
US20080318815A1 (en) * 2007-06-20 2008-12-25 Chevron Oronite Company Llc Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a dairylamine
EP2009082A2 (fr) 2007-06-20 2008-12-31 Chevron Oronite Company LLC Composition d'huile lubrifiante synergique contenant un mélange de diarylamine substituée de nitro et diarylamine
US7683017B2 (en) 2007-06-20 2010-03-23 Chevron Oronite Company Llc Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a diarylamine
US8623798B2 (en) 2007-12-20 2014-01-07 Chevron Oronite Company Llc Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant
US20100152079A1 (en) * 2007-12-20 2010-06-17 Chevron Oronite Company Llc Lubricating oil compositions containing a tetraalkyl-napthalene-1,8 diamine antioxidant
EP2077315A1 (fr) 2007-12-20 2009-07-08 Chevron Oronite Company LLC Compositions d'huile de lubrification contenant un antioxydant de diamine Tetraalkyl-Napthalène-1,8
US20110124538A1 (en) * 2008-08-08 2011-05-26 Albemarle Corporation Octylated Phenyl-Alpha-Naphthylamine Product Mixtures And Production Of Such Mixtures Having A High Content Of Octylated Phenyl-Alpha-Naphthylamine
US20160152789A1 (en) * 2013-07-11 2016-06-02 Nok Corporation Nitrile rubber composition
WO2016123717A1 (fr) * 2015-02-06 2016-08-11 University Of Ottawa Antioxydants et procédés pour maximiser les performances
US10323017B2 (en) 2015-02-06 2019-06-18 Alma Mater Studiorum—Universita di Bologna Antioxidants and methods to maximize performance
US12168726B2 (en) 2018-11-30 2024-12-17 Si Group, Inc. Antioxidant compositions
CN116601263A (zh) * 2020-11-17 2023-08-15 松原实业有限公司 性能提高的包含烷基化二苯胺的组合物
JP2023548936A (ja) * 2020-11-17 2023-11-21 ソンウォン インダストリアル カンパニー リミテッド 改善された特性を有するアルキル化ジフェニルアミンを含む組成物
WO2022108298A1 (fr) * 2020-11-17 2022-05-27 Songwon Industrial Co., Ltd. Compositions comprenant des diphénylamines alkylées présentant des propriétés améliorées
US12203045B2 (en) 2020-11-17 2025-01-21 Songwon Industrial Co., Ltd. Compositions comprising alkylated diphenylamines with improved properties
TWI902970B (zh) * 2020-11-17 2025-11-01 韓商松原產業股份有限公司 包含烷基化二苯胺之具有改良性質的組合物
US12486467B2 (en) 2021-06-25 2025-12-02 Songwon Industrial Co., Ltd. O-alkylated sterically hindered antioxidants

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FR2038396A1 (fr) 1971-01-08
GB1236740A (en) 1971-06-23
DE2017253A1 (de) 1970-10-15
BE748783A (fr) 1970-10-12
NL7005208A (fr) 1970-10-13

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