CA1165314A - Stabilization of hydrocarbon oils with certain dihydroxy components - Google Patents
Stabilization of hydrocarbon oils with certain dihydroxy componentsInfo
- Publication number
- CA1165314A CA1165314A CA000386034A CA386034A CA1165314A CA 1165314 A CA1165314 A CA 1165314A CA 000386034 A CA000386034 A CA 000386034A CA 386034 A CA386034 A CA 386034A CA 1165314 A CA1165314 A CA 1165314A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- weight
- dihydroxy component
- hydrocracked
- equal
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/04—Hydroxy compounds
- C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
- C10M129/14—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring containing at least 2 hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
Abstract
STABILIZATION OF HYDROCRACKED OILS WITH CERTAIN DIHYDROXY COMPONENTS ABSTRACT OF THE DISCLOSURE Hydrocracked lubricating oils are effectively stabilized against deterioration caused by light by the inclusion of at least one of certain dihydroxy components. Such component, e.g., 3,5-di-tert-butyl catechol and 4,6-di-tert-butyl resorcinol, provide outstanding inhibition to sunlight deterioration.
Description
The in~ention rel~te~ ~o a method of ~tabilizing d hydroc~a~ked oil~ ~ore particularly 7 ~t relate~
ts ~t~bil izinq ~c~ ga~t light de~eri~ration ~y ~dding there~ a l~as~ one Q~ certain ~i~ydroxy-components.
~ t i8 ~tlDWll that Dils in qeneral will degrade~l~wly in the pre~ence of light. Oil~ ~uch as ~he ~c~nomica~ly v~lu~ble hydrocra~ed lubricating oils used in hi~ invention, degrade in li~ht, especially in the Dre~ence of air. Since the hydrocracked oils are valuable, there has been considerable effort to ~ind ways to prevent their breakdown due to light.
U.S. Patent 4,036,770 ~eaches a method for stabilizing hydrocracked oils which in~olves a~din~
nitro-containing aromatic amine c~mponent~. Such com~onents ~re relatively expensive and therefore m~y ~dd significantly to the cost of the hydrocracked oils, Also~ such r~mponents m~y impart a less than desirable ~olor an~/or odor to the final product.
U~S. Patent 4,101,430 teache~ that oxidative ~egradation of lu~ricant co~po~ition6 containing certain organo ~ulfur-c~ntaining nickel complexe~ is inhibited.
U.S. Patent~ 2,78~,18~ and 3,156,543 teach the use ~f 3,3',5,5'-tetra alkyl-4t4~dihydroxy diphenyls as o~idation ~tabilizer~ f~r hydr~Garbon fuels, ~uch as gasoline. U.5. Pate~t 3,156,543 discloses ~ha~
~,4'~ (2-i~oprop~1-6 tert-butylphen~ s a light yellow crystalline ~ub~thnce ~nd i~ highly soluble in gasoline, ~iesel fuel and lu~ricating oil. ~owever, ~either of the~e xeferences teach either inhlbiti~
~f ~eterior~tion from livht expvsure ~r hydrocracked lubricatiQg oil~.
~6,'~
One ~ject of the present inventi~n ih to pr~Yide an improved me~hod for ~tabilizin~ hydrocracke~
lu~ricating ~ gain~ e aeteriorating effects Df light~
AnDther object Or the inventi~n i~ -to provi~e an impr~e CDm~iti~n o~ matter in~olvin~ a hydrocracked ?ubricating ~i~ ~hich has improved inhibi~ion again~t deteriorati~n by light, Othes ~jects and advantages Df the present invention will ~ecome apparent hereinafter.
An improved hydrocracked oil compo~ition ha now been discovered. This com~osition comprises a major amount, preferably at least about 70%, by weight of a hydrocracked lubricating ~il an2 a minor amoun~ by weigh~ ~f at least one added dihydroxy ~omponent havin~ a 6tructure:
;
lOH , (H)b 3_OH
~R) a wherein each R is in~ependently selecte~ from the group consisting o~ ~ubstantially monovalent hydrocarbonaceous radicals containing 1 to abollt 24, pre~erably 1 to-~be~ut 1~ and more prefer~bly 1 to about 10, carbon atoms; and a and b are integers such that a is e~aual to at least 2, preferably equal to 2, and the sum of a plus b equals 4.
~ t is preferred that th~ hydrocarbonaceous radical ~e ~ubstantially ~atura ed aliphatic radicals.
~ ~ 6~
Also, it is pxeferred that each of the R qrou~s include at least ~ne textiary carbon atomO More preerably, each of the R sroups has the same structure and, still more preferab~y, each of the R groups i.s a tertiary butyl group.
In a preferred emboaiment, the a~de~ dihydroxy-diphenyl component compri~es about O . 005~ to ~bout 2 . 0%
more preferably, ab~ut 0.01% to about 1. 0%, by weight of the total composition.
lQ The term "hydrocracked lubricating oil~ means an oil, preferably a mineral oil, of lubricating viscosity which is derived from a lubricating oil produced by contac~ing a hydrocarhon feédstoc~ with hydrogen, preferably : in the presence of ca~alyst effective to promote hydro cracking, at hydrocarbon hydrocracking conditions to ~: produce an oil of lubricating viscosity having an increased viscosity index relative to the visc~sity index of : the hydrocarbon feedstock. In addition, the hydrocracked lubricating oll may be subjected ~o addi~ional processing, e.g., further contacting with hydrogen-~: a~ain preferably in the ~resence of an effective catalyst-~
other purifying procedures and the like, to further : ~mprove the guality, e~g~ 9 color, of the hydrocracked lu~ricatinq oil, For example, hydrocracked lubricatin~
oils useful in the present inventi~n may be obtaine~
by the processes disclosed in U.S. Patent 3,642J610.
~ ypical examples of the ~ubstantially monovalent hydrocarb~naceous radical~ from which R may be selected incluaes alkyl,such a~ methyl, ethyl, propyl, butyl, pentyl~ hexyl gincluding cyclohexyl), 05tvl, decyl, the like; ~yl, ~uch ~ phenyl~ benzyl and the like;
alkaryl ~u~h a~ ~ethy~ phenyl, ethyl phenyl, butyl phenyl, octyl ph~yl, ~ea~l phenyl And ghe like;
alkenaryl ~ch ~ e~hylenyl phenyl, octenyl phenyl, oleyl phenyl and the like; ~ralkyl ~uch as ph~nyl ethyl, phenyl o~tyl, phen~l stearyl a~d *he like; and ar~lkenyl ~uch as phenyl ~thylenyl, p~enyl butenyl, phenyl octenyl, phenyl oleyl and ~he like. ~s no~ed above, it is preferred that such hydrocarbonaceous radical~ be substantially 10 ~aturated.
By n substantially hydrocarbonaceo~s~ radical is meant those radical~ which are comp~sed mainly of hydro~en and carbon, and include such radicals ;~
which contain, in addition, minor amounts of ubstituents, such as chlorine, bromine, ~ulfur, nitrogen and the like, which do not substantially affect their hydrocarbon characterO Preferably, such substantial.ly hydrocarbonaceous radical~ include only ~rbon ~nd hydrogen ~toms.
The presen ly useful dihydroxy component m~y be produced using procedures well known in the art.
The following example~ illustrate ~ore ~lear~y the compositions and methods Df the present invention, ~owever, the6e illustra~ion~ 2re not to be interpreted ~pecific limitationfi on this inventicn.
EXAMæLES
These exam~les illustrate certain of the advantages of the present invention.
A commercially available hydrocracked oil of lubricating viscosity was selected for testing.
~his hydrocracked oil had the following properties.
Initial Boiling Point, F. ;~ 600 Viscosity, SU5 at 100~. 156.0 Viscosity Index 106 t~
This oil was deriv~d using a well known lube oil hydrocracking process.
Varying amounts of 3~-di-tert-~uty~ catechol were blended into samples of the hydrocracked ~il.
In order ~o ~etern~ine .he susce?tibi~.ity ~f the oils ~n~ ~len~ to lig~t deterioration, 10 gram ~amples were p~aced In ~5D ml. beaker~ ana exposed to tw~ 12) 275 watt ~.V~ ~unlamps at se~en(7) in~hes ~n a r~tating table ~r a period of fifteen (15) hours.
After the fifteen (15~ ~our exposure periodr each of the samples was processed to determine the amount of E~l~ds Isludge) formation. The followi~ results were obtained:
ydrocracked Oil 3,5-di-tert- Solids ~fter Exposure butyl catechol mg.~ oil weight percent Sample 1 0.00 1.23
ts ~t~bil izinq ~c~ ga~t light de~eri~ration ~y ~dding there~ a l~as~ one Q~ certain ~i~ydroxy-components.
~ t i8 ~tlDWll that Dils in qeneral will degrade~l~wly in the pre~ence of light. Oil~ ~uch as ~he ~c~nomica~ly v~lu~ble hydrocra~ed lubricating oils used in hi~ invention, degrade in li~ht, especially in the Dre~ence of air. Since the hydrocracked oils are valuable, there has been considerable effort to ~ind ways to prevent their breakdown due to light.
U.S. Patent 4,036,770 ~eaches a method for stabilizing hydrocracked oils which in~olves a~din~
nitro-containing aromatic amine c~mponent~. Such com~onents ~re relatively expensive and therefore m~y ~dd significantly to the cost of the hydrocracked oils, Also~ such r~mponents m~y impart a less than desirable ~olor an~/or odor to the final product.
U~S. Patent 4,101,430 teache~ that oxidative ~egradation of lu~ricant co~po~ition6 containing certain organo ~ulfur-c~ntaining nickel complexe~ is inhibited.
U.S. Patent~ 2,78~,18~ and 3,156,543 teach the use ~f 3,3',5,5'-tetra alkyl-4t4~dihydroxy diphenyls as o~idation ~tabilizer~ f~r hydr~Garbon fuels, ~uch as gasoline. U.5. Pate~t 3,156,543 discloses ~ha~
~,4'~ (2-i~oprop~1-6 tert-butylphen~ s a light yellow crystalline ~ub~thnce ~nd i~ highly soluble in gasoline, ~iesel fuel and lu~ricating oil. ~owever, ~either of the~e xeferences teach either inhlbiti~
~f ~eterior~tion from livht expvsure ~r hydrocracked lubricatiQg oil~.
~6,'~
One ~ject of the present inventi~n ih to pr~Yide an improved me~hod for ~tabilizin~ hydrocracke~
lu~ricating ~ gain~ e aeteriorating effects Df light~
AnDther object Or the inventi~n i~ -to provi~e an impr~e CDm~iti~n o~ matter in~olvin~ a hydrocracked ?ubricating ~i~ ~hich has improved inhibi~ion again~t deteriorati~n by light, Othes ~jects and advantages Df the present invention will ~ecome apparent hereinafter.
An improved hydrocracked oil compo~ition ha now been discovered. This com~osition comprises a major amount, preferably at least about 70%, by weight of a hydrocracked lubricating ~il an2 a minor amoun~ by weigh~ ~f at least one added dihydroxy ~omponent havin~ a 6tructure:
;
lOH , (H)b 3_OH
~R) a wherein each R is in~ependently selecte~ from the group consisting o~ ~ubstantially monovalent hydrocarbonaceous radicals containing 1 to abollt 24, pre~erably 1 to-~be~ut 1~ and more prefer~bly 1 to about 10, carbon atoms; and a and b are integers such that a is e~aual to at least 2, preferably equal to 2, and the sum of a plus b equals 4.
~ t is preferred that th~ hydrocarbonaceous radical ~e ~ubstantially ~atura ed aliphatic radicals.
~ ~ 6~
Also, it is pxeferred that each of the R qrou~s include at least ~ne textiary carbon atomO More preerably, each of the R sroups has the same structure and, still more preferab~y, each of the R groups i.s a tertiary butyl group.
In a preferred emboaiment, the a~de~ dihydroxy-diphenyl component compri~es about O . 005~ to ~bout 2 . 0%
more preferably, ab~ut 0.01% to about 1. 0%, by weight of the total composition.
lQ The term "hydrocracked lubricating oil~ means an oil, preferably a mineral oil, of lubricating viscosity which is derived from a lubricating oil produced by contac~ing a hydrocarhon feédstoc~ with hydrogen, preferably : in the presence of ca~alyst effective to promote hydro cracking, at hydrocarbon hydrocracking conditions to ~: produce an oil of lubricating viscosity having an increased viscosity index relative to the visc~sity index of : the hydrocarbon feedstock. In addition, the hydrocracked lubricating oll may be subjected ~o addi~ional processing, e.g., further contacting with hydrogen-~: a~ain preferably in the ~resence of an effective catalyst-~
other purifying procedures and the like, to further : ~mprove the guality, e~g~ 9 color, of the hydrocracked lu~ricatinq oil, For example, hydrocracked lubricatin~
oils useful in the present inventi~n may be obtaine~
by the processes disclosed in U.S. Patent 3,642J610.
~ ypical examples of the ~ubstantially monovalent hydrocarb~naceous radical~ from which R may be selected incluaes alkyl,such a~ methyl, ethyl, propyl, butyl, pentyl~ hexyl gincluding cyclohexyl), 05tvl, decyl, the like; ~yl, ~uch ~ phenyl~ benzyl and the like;
alkaryl ~u~h a~ ~ethy~ phenyl, ethyl phenyl, butyl phenyl, octyl ph~yl, ~ea~l phenyl And ghe like;
alkenaryl ~ch ~ e~hylenyl phenyl, octenyl phenyl, oleyl phenyl and the like; ~ralkyl ~uch as ph~nyl ethyl, phenyl o~tyl, phen~l stearyl a~d *he like; and ar~lkenyl ~uch as phenyl ~thylenyl, p~enyl butenyl, phenyl octenyl, phenyl oleyl and ~he like. ~s no~ed above, it is preferred that such hydrocarbonaceous radical~ be substantially 10 ~aturated.
By n substantially hydrocarbonaceo~s~ radical is meant those radical~ which are comp~sed mainly of hydro~en and carbon, and include such radicals ;~
which contain, in addition, minor amounts of ubstituents, such as chlorine, bromine, ~ulfur, nitrogen and the like, which do not substantially affect their hydrocarbon characterO Preferably, such substantial.ly hydrocarbonaceous radical~ include only ~rbon ~nd hydrogen ~toms.
The presen ly useful dihydroxy component m~y be produced using procedures well known in the art.
The following example~ illustrate ~ore ~lear~y the compositions and methods Df the present invention, ~owever, the6e illustra~ion~ 2re not to be interpreted ~pecific limitationfi on this inventicn.
EXAMæLES
These exam~les illustrate certain of the advantages of the present invention.
A commercially available hydrocracked oil of lubricating viscosity was selected for testing.
~his hydrocracked oil had the following properties.
Initial Boiling Point, F. ;~ 600 Viscosity, SU5 at 100~. 156.0 Viscosity Index 106 t~
This oil was deriv~d using a well known lube oil hydrocracking process.
Varying amounts of 3~-di-tert-~uty~ catechol were blended into samples of the hydrocracked ~il.
In order ~o ~etern~ine .he susce?tibi~.ity ~f the oils ~n~ ~len~ to lig~t deterioration, 10 gram ~amples were p~aced In ~5D ml. beaker~ ana exposed to tw~ 12) 275 watt ~.V~ ~unlamps at se~en(7) in~hes ~n a r~tating table ~r a period of fifteen (15) hours.
After the fifteen (15~ ~our exposure periodr each of the samples was processed to determine the amount of E~l~ds Isludge) formation. The followi~ results were obtained:
ydrocracked Oil 3,5-di-tert- Solids ~fter Exposure butyl catechol mg.~ oil weight percent Sample 1 0.00 1.23
2 0.01 1.01 20 3 0.025 0.94 4 ~.05 ~.77 0.10 0 55 6 0.15 0.36 7 0.20 0.30 8 0.40 ~.16 9 0.70 0.~8 1~ ~.00 0.07 A series of fi~e additional compositions were blended using the hydrocracked oil noted abo~e and 4,6-di-tert-~utyl resorcinol. These five compositions were tested using the above described procedure and the following results were obtained:
~6~3~
4,6 di-tert- ~Glids After Exposure buty~ re~orc~nol _ m~ m. oil ~ . .
0.20 0.43 1~ 0.40 ~.11 12 0.60 0.02 13 0.~0 0.00 14 ~.0~ 0.01 These results indicate that hydrocracked lubricating oll alone is susceptible: to deterioration by sunlight.
~ he dihydroxy components, as set forth in the present in~ention, are shown to provide ~ubstantial inhibition of deterioration of hydrocracked oil by sunlight.
In addition, such dihydroxy components impart little or no distaste~ul odor ~o the hydrocracked oil compositions.
This is in significant contrask to ~and is a substantial benefit relative to) compositions which include various of the nitrogen-containing materials which have been suggested 20 ~y the prior art for inhibiting light deterioration of h hydrocxacked oils~ .
. While this invention has been described with respect ~o various specific examples and embodiments, it is to be understood that the inventisn is not limited thereto : ~ and that it can be variously pra~ticed within the ~cope ~ f the fO11DWing claims:
~6~3~
4,6 di-tert- ~Glids After Exposure buty~ re~orc~nol _ m~ m. oil ~ . .
0.20 0.43 1~ 0.40 ~.11 12 0.60 0.02 13 0.~0 0.00 14 ~.0~ 0.01 These results indicate that hydrocracked lubricating oll alone is susceptible: to deterioration by sunlight.
~ he dihydroxy components, as set forth in the present in~ention, are shown to provide ~ubstantial inhibition of deterioration of hydrocracked oil by sunlight.
In addition, such dihydroxy components impart little or no distaste~ul odor ~o the hydrocracked oil compositions.
This is in significant contrask to ~and is a substantial benefit relative to) compositions which include various of the nitrogen-containing materials which have been suggested 20 ~y the prior art for inhibiting light deterioration of h hydrocxacked oils~ .
. While this invention has been described with respect ~o various specific examples and embodiments, it is to be understood that the inventisn is not limited thereto : ~ and that it can be variously pra~ticed within the ~cope ~ f the fO11DWing claims:
Claims (19)
1. A composition of matter comprising a major amount by weight of a hydrocracked lubricating oil and a minor amount by weight of at least one added dihydroxy component having a structure:
wherein each R is independently selected from the group consisting of substantially monovalent hydrocarbonaceous radicals containing 1 to about 24 carbon atoms, and a and b are integers such that a is equal to at least 2 and the sum of a plus b equals 4.
wherein each R is independently selected from the group consisting of substantially monovalent hydrocarbonaceous radicals containing 1 to about 24 carbon atoms, and a and b are integers such that a is equal to at least 2 and the sum of a plus b equals 4.
2. The composition of claim 1 wherein said hydrocracked lubricating oil comprises at least about 70% by weight of said composition.
3. The composition of claim 2 wherein said R's are independently selected from the group consisting of substantially aliphatic hydrocarbonaceous radicals.
4. The composition of claim 2 wherein said added dihydroxy component comprises about 0.005% to about 2.0% by weight of said composition.
5. The composition of claim 3 wherein said dihydroxy component comprises about 0.01% to about 1.0% by weight of said composition.
6. The composition of claim 3 wherein a is equal to 2 and said dihydroxy component comprises about 0.01% to about 1.0% by weight of said composition.
7. The composition of claim 3 wherein said R's are substantially saturated.
8. The composition of claim 6 wherein each of said R's includes at least one tertiary carbon atom.
9. The composition of claim 3 wherein each of said R's has the same structure and contains 1 to about 10 carbon atoms.
10. The composition of claim 8 wherein each of the R's is tertiary butyl.
11. A method of inhibiting a hydrocracked lubricating oil from deterioration caused by sunlight comprising combining with said oil an inhibiting amount of at least one dihydroxy component having a structure:
wherein each R is independently selected from the group consisting of substantially monovalent hydrocarbonaceous radicals containing 1 to about 24 carbon atoms, and a and b are integers such that a is equal to at least 2 and the sum of a plus b equals 4.
wherein each R is independently selected from the group consisting of substantially monovalent hydrocarbonaceous radicals containing 1 to about 24 carbon atoms, and a and b are integers such that a is equal to at least 2 and the sum of a plus b equals 4.
12. The method of claim 11 wherein said R's are independently selected from the group consisting of substantially aliphatic hydrocarbonaceous radicals.
13. The method of claim 11 wherein said dihydroxy component comprises about 0.005% to about 2.0% by weight of said composition.
14. The method of claim 11 wherein said dihydroxy component is present in an amount equal to about 0.01% to about 1.0% by weight of said composition.
15. The method of claim 12 wherein a is equal to 2 and said dihydroxy component comprises about 0.01% to about 1.0% by weight of said composition.
16. The method of claim 12 wherein said R's are substantially saturated.
17. The method of claim 15 wherein each of said R's includes at least one tertiary carbon atom.
18. The method of claim 16 wherein each of said R's has the same structure and contains 1 to about 10 carbon atoms.
19. The method of claim 17 wherein each of said R's is a tertiary butyl radical.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21042780A | 1980-11-25 | 1980-11-25 | |
| US210,427 | 1980-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1165314A true CA1165314A (en) | 1984-04-10 |
Family
ID=22782866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000386034A Expired CA1165314A (en) | 1980-11-25 | 1981-09-16 | Stabilization of hydrocarbon oils with certain dihydroxy components |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS57135896A (en) |
| BR (1) | BR8107239A (en) |
| CA (1) | CA1165314A (en) |
| GB (1) | GB2087923B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4708809A (en) * | 1982-06-07 | 1987-11-24 | The Lubrizol Corporation | Two-cycle engine oils containing alkyl phenols |
| US4740321A (en) * | 1982-06-07 | 1988-04-26 | The Lubrizol Corporation | Two-cycle engine oils containing sulfurized alkyl phenols |
| US4724091A (en) * | 1983-03-31 | 1988-02-09 | The Lubrizol Corporation | Alkyl phenol and amino phenol compositions and two-cycle engine oils and fuels containing same |
-
1981
- 1981-09-16 CA CA000386034A patent/CA1165314A/en not_active Expired
- 1981-10-26 JP JP17025781A patent/JPS57135896A/en active Pending
- 1981-11-09 BR BR8107239A patent/BR8107239A/en unknown
- 1981-11-23 GB GB8135282A patent/GB2087923B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2087923A (en) | 1982-06-03 |
| JPS57135896A (en) | 1982-08-21 |
| BR8107239A (en) | 1982-07-27 |
| GB2087923B (en) | 1984-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20010410 |